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

HRID 1921632Notes

Reaction equation

HRID 1921632 reaction equation
COC(=O)C.[F:6][C:7]([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:8](O)=[O:9].[NH2:22][NH2:23]>CO>[F:6][C:7]([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:8]([NH:22][NH2:23])=[O:9]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131729218HCID 131729218, compound

Product 1

HCID 589552502,2-Difluoro-2-(quinolin-6-yl)acetohydrazideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of difluoro-quinolin-6-acetic acid methyl acetate (670 mg, 2.83 mmol) in methanol (20 mL) was added anhydrous hydrazine (2 mL). The mixture heated to reflux for 2 h, cooled to room temperature, concentrated and dried in high vacuum to give a light orange solid (680 mg, 100%). 1H-NMR (DMSO): δ 9.02-9.01 (1H, dd, J=1.7 Hz), 8.56-8.54 (1H, d, J=9.3 Hz), 8.28 (1H, s), 8.17-8.15 (1 H, d, J=8.8 Hz), 7.91-7.88 (1H, dd, J=2.0, 2.0 Hz), 7.66-7.63 (1H, q, J=4.0 Hz).

Workup

  1. temperatureThe mixture heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-72c1160af15e4ffa97fa99b90611e706
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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