Ethyl Acetate → 5-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582011

Reaction equation

HRID 582011 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.[C:18]1([NH:28][NH2:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:2][C:1]1[N:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:29]=[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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 543553485-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamideYield 27%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (464 mg, 2.0 mmol), 1-naphthyl hydrazine hydrochloride (389 mg, 2.0 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 50-60% ethyl acetate in hexane) and was recrystallised from diethylether to give the title compound as pink crystals (185 mg) m.p. 195°. δH (CDCl3) 8.00 (1H, d, J 8.3 Hz), 7.95 (1 H., m), 7.73-7.55 (7H, m), 7.30 (2H, d, J 8.3 Hz), 5.52 (2H, br s), 5.16 (2H, br s) and 2.42 (3H, s).

Workup

  1. customwas recrystallised from diethylether

Sources & evidence

ORD record
ord-ef930def809749ab9ca3e9e30e78bcdb
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Linked notes

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