Hydrazine hydrate (1:1) → HCID 67083984, compound

HRID 79027Notes

Reaction equation

HRID 79027 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][C:13]=2[F:20])[C:3]=1[CH:21]=O.O.[NH2:24][NH2:25]>COCCOC>[F:20][C:13]1[CH:14]=[C:15]([S:18][CH3:19])[CH:16]=[CH:17][C:12]=1[NH:11][C:4]1[C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=[C:2]2[C:3]=1[CH:21]=[N:24][NH:25]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866562374-Fluoro-2-(2-fluoro-4-methylsulfanyl-phenylamino)-3-formyl-benzoic acid

Product 1

HCID 67083984HCID 67083984, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-fluoro-2-(2-fluoro-4-methylsulfanyl-phenylamino)-3-formyl-benzoic acid (105 mg, 0.32 mmol) in DME (5 mL) was added hydrazine hydrate (5 mL) and the reaction mixture heated at 90° C. for 18 hours. The volatile solvent was removed in vacuo and the residue acidified with concentrated HCl whilst applying cooling. The resultant precipitate was collected by filtration and washed with water to give the title compound as a tan solid (85 mg, 82%). LCMS (Method B) RT 3.12 [M+H]+ 318.

Workup

  1. customThe volatile solvent was removed in vacuo
  2. temperaturewhilst applying cooling
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-0fdb007c69104fa0a5cb5b6cc2588bbd
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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