Hydrochloric Acid → 2,2-Difluoro-2-(quinolin-6-yl)acetohydrazide

HRID 2388094Notes

Reaction equation

HRID 2388094 reaction equation
[F:1][C:2]([F:18])([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)[C:3](OCC)=[O:4].[NH2:19][NH2:20].Cl>C(O)C>[F:1][C:2]([F:18])([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)[C:3]([NH:19][NH2:20])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 28242385Ethyl 2,2-difluoro-2-(quinolin-6-yl)acetate

Product 1

HCID 589552502,2-Difluoro-2-(quinolin-6-yl)acetohydrazideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As shown in step 3-ii in Scheme 3, compound 1009 (10.0 g, 39.80 mmol) was dissolved in ethanol (100 mL), hydrazine (7.65 g, 7.50 mL, 239 mmol) was added, and the reaction mixture was stirred at room temperature for 10 minutes. After pouring the mixture into 2N HCl solution, the aqueous mixture was washed twice with DCM and the pH was adjusted to 8 while bubbling nitrogen gas through the solution. The resulting aqueous solution was exhaustively extracted with DCM (10×) and the combined organics dried over MgSO4, filtered, and the volatiles removed under reduced pressure to provide 2,2-difluoro-2-(quinolin-6-yl)acetohydrazide as a yellow solid (compound 1010, 91% yield). This compound that was used directly without further purification.

Workup

  1. washthe aqueous mixture was washed twice with DCM
  2. customwhile bubbling nitrogen gas through the solution
  3. extractionThe resulting aqueous solution was exhaustively extracted with DCM (10×)
  4. dry with materialthe combined organics dried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-5ac88dda66054c54aac06f987c487ffd
Source dataset
uspto-grants-2012_09
Patent number
US08269013B2

Reaction notes

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