Aniline → HCID 19799476, compound

HRID 2081236Notes

Reaction equation

HRID 2081236 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([OH:12])[C:4]=1[C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([OH:12])[C:4]=1[C:13](=[N:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 19799481HCID 19799481, compound

Product 1

HCID 19799476HCID 19799476, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-cyano-2-benzoyl-1-hydroxy-indole (2.62 g, 10.0 mmole) and aniline (1.0 g, 10.8 mmole) were heated at reflux in toluene (50 ml) under a trap for 16 hours. Concentration in vacuo afforded a solid. Recrystallization from methylcyclohexane provided dark crystals, m.p. 188°-190° C. Analysis (dry 25° C.): Fd(calculated) N, 12.2 (12.4), C, 78.2 (78.3) H, 4.7 (4.5).

Workup

  1. temperaturewere heated
  2. concentrationConcentration in vacuo
  3. customafforded a solid
  4. customRecrystallization from methylcyclohexane provided dark crystals, m.p. 188°-190° C
  5. customAnalysis (dry 25° C.)

Sources & evidence

ORD record
ord-fe9bf1fdfcb04cffbd6729957f808d5c
Source dataset
uspto-grants-1993_02
Patent number
US05183894

Reaction notes

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