Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-butyl-1-(2-chlorophenyl)-1H-pyrazol-5-amine

HRID 631697Notes

Reaction equation

HRID 631697 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[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:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 70164923-tert-butyl-1-(2-chlorophenyl)-1H-pyrazol-5-amineYield 65.3%

Procedure

Following the procedure in Example 161A Step 3, 2-chlorophenylhydrazine hydrochloride (1.43 g, 8.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.0 g, 8.0 mmol) were reacted to give 3-tert-butyl-1-(2-chlorophenyl)-1H-pyrazol-5-amine (1.30 g, 5.22 mmol, 65%). 1H NMR (300 MHz, DMSO-d6) δ 7.60 (d, 1H), 7.48-7.42 (m, 3H), 5.28 (s, 1H), 4.94 (s, 2H), 1.19 (s, 9H); LC-MS (ESI) m/z 250 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1333801121be45d0a48be9f83b560de6
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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