Hydrazine hydrate (1:1) → 2,2-Difluoro-2-(quinolin-6-yl)acetohydrazide

HRID 1921635Notes

Reaction equation

HRID 1921635 reaction equation
C([O:3][C:4](=O)[C:5]([F:17])([F:16])[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)C.[NH2:19][NH2:20].O>CO>[F:16][C:5]([F:17])([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)[C:4]([NH:19][NH2:20])=[O:3]

Participants

4

Reactant 2

HCID 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 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of difluoro-quinolin-6-yl-acetic acid ethyl ester (5.5 g, 21.9 mmol) in methanol (85 mL) was added hydrate hydrazine (5.3 mL, 109.5 mmol). The mixture was heated to 45° C. for 10 min., cooled to room temperature, concentrated, and taken up in dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give a light orange solid (4.4 g, 85%).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e2c15ea82a0461390023d2b39dc5b00
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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