Aniline → HCID 18962905, compound

HRID 1194710Notes

Reaction equation

HRID 1194710 reaction equation
[C:1]([CH:3]([C:9]([C:11]1[C:12]2[CH2:25][O:24][C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[C:13]=2[N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1)=[O:10])[C:4](OCC)=[O:5])#[N:2].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C(C)=CC=CC=1>[C:1]([CH:3]([C:9]([C:11]1[C:12]2[CH2:25][O:24][C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[C:13]=2[N:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1)=[O:10])[C:4]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 86742838HCID 86742838, compound

Product 1

HCID 18962905HCID 18962905, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Cyano-3-(1,4-dihydro-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-propanoic acid, ethyl ester (1.2 g) is reacted with aniline (1.1 g) in xylene (100 ml) at the reflux temperature for 48 hours. After cooling the precipitate is filtered and washed with xylene, then crystallized from dichloromethane/methanol to give 0.7 g of 2-cyano-3-(1,4-dihydro-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 280°-282° C.

Workup

  1. temperatureAfter cooling the precipitate
  2. filtrationis filtered
  3. washwashed with xylene
  4. customcrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-1f063ad6607c406ba1caaa2bc27ab726
Source dataset
uspto-grants-1989_03
Patent number
US04816467

Reaction notes

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