Ammonia → HCID 67004761, compound

HRID 217142Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]([N+:13]([O-:15])=[O:14])=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:7]=1.[NH3:17]>C(O)C.CO>[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([NH2:17])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(5-bromo-3-fluoro-2-nitro-phenyl)-1H-pyrazole (240 mg, 0.84 mmol) in ethanol (3 mL) was added ammonia (3 mL, 2N in methanol. The resulting mixture was heated in a sealed tube at 80° C. for 16 hours then concentrated in vacuo. The residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:3) to afford 205 mg (86%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 5.20 (br s, 2H), 6.50 (t, 1H), 6.9 (d, 1H), 7.1 (d, 1H), 7.7 (d, 1H), 7.8 (d, 1H). MS M+1 283, M+1+2 285.

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by column chromatography over silica gel
washeluted with ethyl acetate:hexanes (1:3)

Sources & evidence

ORD record: ord-c69ea3be25d245a7bfcfd2e770fb0ee6
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193352B2

Reaction notes

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