HCID 66869089, compound → HCID 66869298, compound

HRID 1519048Notes

Reaction equation

HRID 1519048 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:20])[C:11]([Cl:19])=[C:12](C(O)=O)[N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:20])[C:11]([Cl:19])=[CH:12][N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66869089HCID 66869089, compound

Product 1

HCID 66869298HCID 66869298, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Benzyloxy)-3-chloro-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (3.50 g, 11.9 mmol) was heated in DMF (10 mL) for one hour. The reaction mixture was concentrated by rotary evaporation and the residue was triturated with ethyl acetate/ether to give 3-(benzyloxy)-5-chloro-1-methylpyridin-4(1H)-one (2.80 g) as a pale brown solid. Yield=94%; 1H NMR (DMSO-D6, 90 MHz) δ (ppm): 8.08 (d, J=1.8 Hz, 1H), 7.68 (d, J=1.8 Hz, 1H), 7.19-7.58 (m, 5H), 5.01 (s, 2H) and 3.67 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. customthe residue was triturated with ethyl acetate/ether

Sources & evidence

ORD record
ord-3a14e8411e1e4e459623a9c5dda69f63
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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