m-Chlorophenylhydrazine hydrochloride → 3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-amine

HRID 631727Notes

Reaction equation

HRID 631727 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=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:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

3

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 29735883-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-amineYield 71.3%

Procedure

The title compound was prepared from 3-chlorophenylhydrazine hydrochloride (1.43 g, 8.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.0 g, 8.0 mmol) using the procedure in Example 161A Step 3 to give 3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-amine (1.42 g, 5.70 mmol, 71%). 1H NMR (300 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.61 (d, 1H), 7.46 (t, 1H), 7.30 (d, 1H), 5.42 (s, 1H), 5.34 (s, 2H), 1.09 (s, 9H); LC-MS (ESI) m/z 250 (M+H)+.

Sources & evidence

ORD record
ord-50d4346f8b4340e286349de9026ce310
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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