Aniline → HCID 178509130, compound

HRID 2095196Notes

Reaction equation

HRID 2095196 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-86a6a196aa6645af9143d8bded02743f
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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