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

HRID 1959647Notes

Reaction equation

HRID 1959647 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.O.[NH2:20][NH2:21]>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:20][NH2:21])=[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 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

Difluoro-quinolin-6-yl-acetic acid ethyl ester (836 mg, 3.33 mmol) was dissolved in MeOH (13 mL). Hydrazine monohydrate (1.5 mL, 16.8 mmol) was added. The mixture was heated at 45° C. for 30 min, cooled to rt, concentrated, and taken up in DCM. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel column to give the title compound as light orange solid (400 mg, 51%). 1H-NMR (400 MHz, CDCl3). ppm 3.99 (br s, 2H), 7.51 (m, 1H), 7.92 (m, 1H), 8.15 (s, 1H), 8.20-8.26 (q, 2H), 9.02 (m, 1H).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product, which
  7. customwas purified by silica gel column

Sources & evidence

ORD record
ord-56f9002025034d21abfbf0d3cab915a4
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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