Sodium Hydroxide → 5-Amino-1-(4-methoxyphenyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582013Notes

Reaction equation

HRID 582013 reaction equation
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1.[OH-].[Na+]>>[NH2:2][C:1]1[N:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[N:27]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 540945005-Amino-1-(4-methoxyphenyl)-3-(4-tolyl)pyrazole-4-carboxamideYield 31.3%

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (232 mg, 1.0 mmol), 4-methoxyphenylhydrazine hydrochloride (192 mg, 1.1 mmol) and sodium hydroxide (44 mg, 1.1 mmol) following the procedure used for the compound of Example 12. The crude product was purified by chromatography (SiO2, 75% ethyl acetate in hexane) and recrystallisation from ethyl acetate-hexane to give the title compound as white crystals (101 mg) m.p. 174-175°. δH (d6DMSO) 7.49-7.43 (4H, m), 7.28 (2H, d, J 7.8 Hz), 7.07 (2H, d, J 8.9 Hz), 6.32 (2H, br s), 3.81 (3H, s) and 2.29 (3H, s), one set of amino protons not observed. MS (ES+) 323 (MH+, 100%).

Workup

  1. customThe crude product was purified by chromatography (SiO2, 75% ethyl acetate in hexane) and recrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2d59d6b97eb6423e9944873b487916d8
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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