Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → 3-(tert-Butyl)-1-(4-chlorophenyl)-1H-pyrazol-5-amine

HRID 1918173Notes

Reaction equation

HRID 1918173 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16]>>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

3

Reactant 2

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 7706493-(tert-Butyl)-1-(4-chlorophenyl)-1H-pyrazol-5-amineYield 33%

Procedure

Following the procedure in Example 161A Step 3, 4-chlorophenylhydrazine hydrochloride (1.43 g, 8.0 mol) and 4,4-dimethyl-3-oxopentanenitrile (1.0 g, 8.0 mmol) were reacted to give 3-tert-butyl-1-(4-chlorophenyl)-1H-pyrazol-5-amine (653 mg, 2.62 mmol, 33%). 1H NMR (300 MHz, DMSO-d6) δ 7.61 (d, 1H), 7.49 (d, 2H), 5.39 (s, 1H), 5.28 (s, 1H), 1.09 (s, 9H); LC-MS (ESI) m/z 250 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-27f16a1fa3254d1db446f11a3aea0895
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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