# US 4,398,030 A · 3-[(Substituted-amino)(aryl)methyl]-1H-indoles

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- Number: US 4,398,030 A
- Document ID: US4398030A
- Status: Granted
- Kind: A
- Application number: 06/341,951
- Filed: 1982-01-22
- Granted: 1983-08-09
- Earliest claimed: 1980-03-06
- Assignees: Sterling Drug Inc.
- Inventors: Paul J. Schmidt; William M. Hung
- Web page: https://patentgrep.com/patent/US4398030A

## CPC

- C07D 209/14: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- B41M 5/136: Organic colour formers, e.g. leuco dyes
- B41M 5/323: Organic colour formers, e.g. leuco dyes
- B41M 5/1366: {characterised solely by tri (aryl or hetaryl)methane derivatives (B41M5/1363 takes precedence)}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)

## Abstract

3-[(Substituted-amino)(aryl or heteroaryl)methyl]-1H-indoles which are useful as color-formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting 3-[(arylsulfonyl)(aryl or heteroaryl)methyl]-1H-indoles with amines or precursors thereof in the presence of a base.

## Claims

### Claim 1

A compound having the formula ##STR12## wherein: R.sub.1 is hydrogen or lower-alkyl;
R.sub.2 is hydrogen, lower-alkyl or phenyl;
R.sub.3 is hydrogen or lower-alkyl;
R.sub.4 is hydrogen, lower-alkyl, benzyl, di-lower-alkyl-amino-lower-alkyl, tri-lower-alkylammonium-lower-alkyl, phenyl, phenyl substituted with 1 or 2 halo, lower-alkyl or lower-alkoxy groups, or NR.sub.3 R.sub.4 is pyrrolidino, piperidino, hexamethyleneimino or morpholino; and
Z is biphenylyl, naphthyl or a substituent having the formula ##STR13## wherein: R.sub.5 and R.sub.6 are independently lower-alkyl or benzyl and
R.sub.7 is hydrogen, lower-alkyl, lower-alkoxy, halo or di-lower-alkylamino.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein Z is a substituent having the formula ##STR14## where R.sub.5, R.sub.6 and R.sub.7 have the meanings given in claim 1.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein R.sub.5 and R.sub.6 are each lower-alkyl and R.sub.7 is hydrogen .

### Claim 4

A compound according to clam 3 wherein R.sub.4 is lower-alkyl, phenyl or phenyl substituted with 1 or 2 halo groups .

### Claim 5 (depends on 3)

A compound according to claim 3 wherein NR.sub.3 R.sub.4 is piperidino or morpholino.

### Claim 6 (depends on 3)

A compound according to claim 3 wherein R.sub.4 is di-lower-alkylamino-lower-alkyl or tri-lower-alkylammonium-lower-alkyl.

### Claim 7 (depends on 4)

3-{(Dimethylamino)[4-(dimethylamino)phenyl]methyl}-1-ethyl-2-methyl -1H-indole according to claim 4.