# US 5,349,090 A · Process for preparing arylketoamines

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- Number: US 5,349,090 A
- Document ID: US5349090A
- Status: Granted
- Kind: A
- Application number: 08/191,849
- Filed: 1994-02-04
- Granted: 1994-09-20
- Earliest claimed: 1994-02-04
- Assignees: Hoechst Celanese Corporation
- Inventors: Ahmed M. Tafesh; George Kvakovszky; Charlet R. Lindley
- Web page: https://patentgrep.com/patent/US5349090A

## CPC

- C07C 221/00: Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and a liquid carboxylic acid at a temperature of less than about 60.degree. C.

## Claims

### Claim 1

In a process for the preparation of arylketoamines from arylisonitrosoalkanones by a catalytic hydrogenation reaction, the improvement which comprises conducting said catalytic hydrogenation reaction at a temperature of less than about 60.degree. C. in a reaction medium consisting essentially of a liquid carboxylic acid.

### Claim 2 (depends on 1)

The process of claim 1 wherein the temperature is from about 10.degree. C. to about 35.degree. C.

### Claim 3 (depends on 1)

The process of claim 1 wherein the liquid carboxylic acid is selected from the group consisting of formic, acetic, propanoic, butyric, valeric, caproic, heptanoic, octanoic, nonanoic, undecanoic, isobutyric, isovaleric, cyclohexane carboxylic acid, and mixtures thereof.

### Claim 4

A method of preparing an arylketoamine, which comprises:
a) providing a compound of the formula ##STR5## wherein, R.sub.1 =an hydroxyl or a C.sub.1 -C.sub.8 alkyloxy radical,
R.sub.2 =hydrogen or a C.sub.1 -C.sub.8 alkyl or cycloalkyl radical, and
Ar substituted or unsubstituted phenyl or a phenyl or naphthyl radical, wherein the substituents are selected from the group consisting of hydroxyl, alkoxy, alkyl, phenyl, and benzyl radicals, wherein the alkyl component is a branched or unbranched C.sub.1 -C.sub.8 alkyl radical, wherein any of said alkyl, phenyl, and benzyl radicals are optionally substituted with one or more substituents selected from hydroxyl, sulfonic acid, and sulfinic acid radicals, and wherein said phenyl and benzyl substituents are optionally substituted with a C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy radical, or both; and
b) reacting said compound with hydrogen in a reaction medium consisting essentially of a liquid carboxylic acid and a hydrogenation catalyst comprising a transition metal catalyst on an inert support, to produce a reaction at a temperature of less than about 60.degree. C. product comprising an arylketoamine as a major compound.

### Claim 5 (depends on 4)

The method of claim 4 in which said liquid carboxylic acid is selected from the group consisting of formic, acetic, propanoic, butyric, valeric, caprotic, heptanoic, octanoic, nonanoic, undecanoic, isobutyric, isovaleric, cyclohexane carboxylic acid, and mixtures thereof.

### Claim 6 (depends on 4)

The method of claim 4, in which the amount of hydrogen reacted in step b) is about two molar equivalents, based on the moles of the compound of said formula of step a).

### Claim 7 (depends on 4)

The method of claim 4, wherein the reaction is carried out under hydrogen pressure ranging from about 1.0 psi to about 300 psi, at temperatures ranging from about 10.degree. C. to about 35.degree. C.

### Claim 8

A method of producing the .alpha.-amino o- or .rho.-hydroxyacetophenone, which comprises the steps of:
a) providing the compound o- or .rho.-hydroxy-.alpha.-isonitrosoacetophenone;
b) reacting at a temperature of less than about 60.degree. C. said compound with hydrogen in a reaction medium consisting essentially of a liquid carboxylic acid and a transition metal catalyst on an inert support.

### Claim 9 (depends on 8)

The method of claim 8, wherein in step b) approximately two moles of hydrogen are reacted per mole of said compound of step a).

### Claim 10 (depends on 9)

The method of claim 9, wherein said transition metal is selected from the group consisting of platinum, palladium, nickel, rhodium, and combinations thereof.

### Claim 11 (depends on 10)

The method of claim 10, wherein said hydrogenation catalyst is palladium.

### Claim 12 (depends on 11)

The method of claim 11, wherein said palladium, excluding said inert support, is present in a quantity ranging from about 0.005% by weight to about 1.5% by weight based on the weight of said compound of step a).

### Claim 13 (depends on 12)

The method of claim 12, wherein the reaction is carried out under hydrogen pressure ranging from about 1.0 psi to about 300 psi, at temperatures ranging from about 10.degree. C. to about 35.degree. C.

### Claim 14 (depends on 13)

The method of claim 13, wherein the o- or .rho.-hydroxyisonitrosoacetophenone is present initially in said reaction medium in an amount ranging from about 5% by weight to about 50% by weight, of said reaction medium, and wherein said supported palladium catalyst is present in said reaction medium at a concentration ranging from about 0.01% by weight to about 10% by weight of said reaction medium.

### Claim 15 (depends on 14)

The method of claim 14, wherein said o- or .rho.-hydroxyisonitrosoacetophenone is present initially in said reaction medium in an amount less than about 30% by weight of said reaction medium.