Hydrazine hydrate (1:1) → (2-Fluoro-4-iodo-phenyl)-(5-nitro-1H-indazol-4-yl)-amine

HRID 79040Notes

Reaction equation

HRID 79040 reaction equation
F[C:2]1[C:7]([CH:8]=O)=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.O.[NH2:23][NH2:24]>COCCOC>[F:18][C:12]1[CH:13]=[C:14]([I:17])[CH:15]=[CH:16][C:11]=1[NH:10][C:6]1[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=[C:2]2[C:7]=1[CH:8]=[N:23][NH:24]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866562386-Fluoro-2-(2-fluoro-4-iodo-phenylamino)-3-nitro-benzaldehyde

Product 1

HCID 67083627(2-Fluoro-4-iodo-phenyl)-(5-nitro-1H-indazol-4-yl)-amineYield 98%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 6-fluoro-2-(2-fluoro-4-iodo-phenylamino)-3-nitro-benzaldehyde (864 mg, 2.14 mmol) in DME (15 ml) was slowly added hydrazine hydrate (10 mL) at room temperature and the reaction mixture stirred for 18 hours. The organic solvent was removed in vacuo and the mixture diluted with water (50 mL). The resulting solid was collected by filtration, washed with water and dried under vacuum to yield the title compound (839 mg, 98%). LCMS (Method B): RT=3.61 min, [M+H]+=399.

Workup

  1. customat room temperature
  2. customThe organic solvent was removed in vacuo
  3. additionthe mixture diluted with water (50 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-edd1d763f8bd491ab56369709c4a27f4
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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