Hydrochloric Acid → 5-(difluoromethyl)pyridin-3-amine

HRID 2244461Notes

Reaction equation

HRID 2244461 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:14]([F:16])[F:15])[CH:13]=1)(C)(C)C.Cl.CCO>C(OCC)(=O)C>[F:15][CH:14]([F:16])[C:12]1[CH:13]=[C:8]([NH2:7])[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 684058001,1-Dimethylethyl N-[5-(difluoromethyl)-3-pyridinyl]carbamate

Product 1

HCID 552855075-(difluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Difluoromethyl-pyridin-3-yl)-carbamic acid tert-butyl ester (0.30 g, 1.2 mmol) was dissolved in 10 ml ethyl acetate and 8M HCl in EtOH (3 ml, 25 mmol) were added. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched by addition of 20 ml sat. NaHCO3 solution and extracted three time with 50 ml ethyl acetate. The organic phases were pooled, dried with sodium sulfate and evaporated. The title compound was obtained as a brown oil (0.158 g, 89%).

Workup

  1. customThe reaction mixture was quenched by addition of 20 ml sat. NaHCO3 solution
  2. extractionextracted three time with 50 ml ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-50acdfd076024512a0153b6513d41238
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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