Hydrazine → 2,2-Difluoro-2-(quinolin-6-yl)acetohydrazide

HRID 469190Notes

Reaction equation

HRID 469190 reaction equation
O.[NH2:2][NH2:3].[F:4][C:5]([F:21])([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[CH:14]2)[C:6](OCC)=[O:7].NN>CC(O)(CC)C>[F:4][C:5]([F:21])([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[CH:14]2)[C:6]([NH:2][NH2:3])=[O:7]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 28242385Ethyl 2,2-difluoro-2-(quinolin-6-yl)acetate

Product 1

HCID 589552502,2-Difluoro-2-(quinolin-6-yl)acetohydrazideYield 92.1%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

To a reactor under inert atmosphere was added 31.05 mL 2-methyl-2-butanol and 12.58 mL (0.259 mol) hydrazine hydrate. Then a solution of 26 g (0.103 mol) ethyl difluoro(quinolin-6-yl)acetate in 125 mL 2-methyl-2-butanol was dosed to the hydrazine solution at room temperature. The precipitate was filtered off from the reaction mixture and was washed with water and dried at 50° C. 22.51 g 2,2-difluoro-2-quinolin-6-ylacetohydrazide was obtained in 90% yield.

Workup

  1. filtrationThe precipitate was filtered off from the reaction mixture
  2. washwas washed with water
  3. customdried at 50° C

Sources & evidence

ORD record
ord-03069ba38aff439a9439dd0979007eab
Source dataset
uspto-grants-2014_01
Patent number
US08629144B2

Reaction notes

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