Aniline → HCID 178509130, compound

HRID 255030Notes

Reaction equation

HRID 255030 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[NH2:10][C:11]1[CH:15]=[CH:14][NH:13][N:12]=1.[NH2:16]C1C=CC=CC=1>O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][N:16]=[C:15]2[CH:14]=[N:13][N:12]=[C:11]2[NH2:10])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 3

HCID 6115AnilineHCID 774693,4-DifluoroanilineHCID 178418806HCID 178418806, compound

Product 1

HCID 178509130HCID 178509130, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine was prepared from 3,4-difluoroaniline (0.62 g, 4.8 mmol) and 3-aminopyrazole (0.4 g, 4.8 mmol) according to the procedure described above except that the aniline was initially dissolved in a mixture of water (7.2 mL) and DMF (1.16 mL) prior to being acidified. The solvents were removed under reduced pressure and the resulting crude material was purified by column chromatography eluting with (CHCl3:MeOH=10:1) to yield 0.41 g (38%) of the compound as a yellow solid. 1H NMR (ppm, 200 MHz, DMSO-d6) δ 12.0 (br s, 1H), 7.2-8.0 (m, 4H), 6.9 (m, 2H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe resulting crude material was purified by column chromatography
  3. washeluting with (CHCl3:MeOH=10:1)

Sources & evidence

ORD record
ord-fe3951d84628403ca3a0b5eb41577cc7
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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