Trifluoroacetic acid → Ammonia

HRID 855604Notes

Reaction equation

HRID 855604 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([NH:16]C(=O)OC(C)(C)C)=[CH:10]1>ClCCl>[NH3:9].[NH2:16][C:11]1[CH:12]=[CH:13][C:14](=[O:15])[N:9]([CH3:8])[CH:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15185799tert-Butyl (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)carbamate

Product 2

HCID 222AmmoniaHCID 102200055-Amino-1-methyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) was added dropwise to an ice-cooled solution of tert-butyl (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)carbamate (Heterocycles 1995; 40; 2; 831-836) (2.87 g, 12.8 mmol) in dichloromethane (80 mL), and the reaction then stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) as eluant to afford the title compound as a red/brown solid, 1.90 g.

Workup

  1. customthe reaction
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-285bf1710d784c79a7fd196feab9f493
Source dataset
uspto-grants-2007_08
Patent number
US07262192B2

Reaction notes

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