Hydrazine hydrate (1:1) → (2-Fluoro-4-iodo-phenyl)-(6-methoxy-5-nitro-1H-indazol-4-yl)-amine

HRID 79046Notes

Reaction equation

HRID 79046 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])=[C:4]([O:22][CH3:23])[CH:3]=1.O.[NH2:25][NH2:26]>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])=[C:4]([O:22][CH3:23])[CH:3]=[C:2]2[C:7]=1[CH:8]=[N:25][NH:26]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86656240HCID 86656240, compound

Product 1

HCID 67083621(2-Fluoro-4-iodo-phenyl)-(6-methoxy-5-nitro-1H-indazol-4-yl)-amineYield 64%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A biphasic mixture of 6-fluoro-2-(2-fluoro-4-iodo-phenylamino)-4-methoxy-3-nitro-benzaldehyde (1.5 g, 3.46 mmol) in hydrazine hydrate (10 mL) and DME (10 mL) was stirred at room temperature for 4 hours, then heated at 50° C. for 3 hours. The reaction mixture was concentrated in vacuo, the residue treated with water and the resultant solid precipitate collected by filtration to give a red/orange solid. The solid was recrystallised from IMS to give the title compound as a yellow solid (956 mg, 64%). LCMS (Method B) RT=3.62 min, [M+H]+=429 [M−H]−=427.

Workup

  1. temperatureheated at 50° C. for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue treated with water
  4. filtrationthe resultant solid precipitate collected by filtration
  5. customto give a red/orange solid
  6. customThe solid was recrystallised from IMS

Sources & evidence

ORD record
ord-7dd3534536b04e0e90910ccfc446f3a7
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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