(4-Nitrophenyl)hydrazine → 5-Amino-1-(4-nitrophenyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582014Notes

Reaction equation

HRID 582014 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([C:14](=[C:18](SC)[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:15]([NH2:17])=[O:16])#[N:13]>>[NH2:13][C:12]1[N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[N:11]=[C:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:14]=1[C:15]([NH2:17])=[O:16]

Participants

3

Reactant 2

HCID 3310889(4-Nitrophenyl)hydrazineHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide

Product 1

HCID 539403975-Amino-1-(4-nitrophenyl)-3-(4-tolyl)pyrazole-4-carboxamide

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acetamide (464 mg, 2.0 mmol) and 4-nitrophenylhydrazine (337 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was purified by column chromatography (SiO2, 2% acetic acid, 5% methanol in CH2Cl2) to give the title compound as a yellow solid (14 mg) m.p. 299-3000. δH (d6DMSO) 8.42 (2H, d, J 8.6 Hz), 8.21 (2H, d, J 8.7 Hz), 7.80 (2H, d, J 8.0 Hz) and 7.75 (2H, d, J 7.9 Hz).

Workup

  1. customThe crude product was purified by column chromatography (SiO2, 2% acetic acid, 5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-5458231892084d6e93c1b587842c4cd6
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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