m-Tolylhydrazine → HCID 21812821, compound

HRID 1504779Notes

Reaction equation

[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][NH2:8])[CH:2]=1.CO[CH:12]=[CH:13][C:14]#[N:15].[O-]CC.[Na+]>C(O)C>[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:12]=[CH:13][C:14]([NH2:15])=[N:8]2)[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

m-Tolylhydrazine (200 mg, 1.64 mmol), 3-methoxyacrylonitrile (0.137 mL, 1.64 mmol), and sodium ethoxide (111 mg, 1.64 mmol) were dissolved in ethanol (8 mL) and stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by silica gel chromatography (ethyl acetate/hexanes, linear gradient) to afford 1-m-tolyl-1H-pyrazol-3-amine. MS ESI calc'd. for C10H12N3 [M+H]+ 174. found 174. 1H NMR (500 MHz, DMSO-d6) δ 8.08 (s, 1H), 7.46 (s, 1H), 7.40 (d, J=8.5 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 5.69 (d, J=2.5 Hz, 1H), 5.01 (s, 2H), 2.31 (s, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
custompurified by silica gel chromatography (ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record: ord-d639398ccf4f4ddb94b84a7c41e1a4ae
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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