m-Tolylhydrazinium(1+) chloride → 1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amine

HRID 631694

Reaction equation

HRID 631694 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[F:11][C:12]([F:19])([F:18])[C:13](=O)[CH2:14][C:15]#[N:16]>>[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:15]([NH2:16])=[CH:14][C:13]([C:12]([F:19])([F:18])[F:11])=[N:9]2)[CH:3]=1

Participants

3

Reactant 2

HCID 71562m-Tolylhydrazinium(1+) chlorideHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 668768041-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amineYield 22%

Procedure

Following the procedure in Example 161A Step 3, m-tolylhydrazine hydrochloride (1.15 g, 7.30 mmol) and 4,4,4-trifluoro-3-oxobutanenitrile (1.0 g, 7.30 mmol) were reacted to give 1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (380 mg, 1.57 mmol, 22%). 1H NMR (300 MHz, DMSO-d6) δ 7.60-7.20 (m, 4H), 5.82-5.61 (m, 3H), 2.59 (s, 3H); LC-MS (ESI) m/z 242 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c8b3db8cbc694778a58b76e34d147e39
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Linked notes

Loading…