Hydrochloric Acid → benzyl 2-ethyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

HRID 15734

Reaction equation

HRID 15734 reaction equation
[O:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)C.[C:9](Cl)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH2:20]([Mg]Br)[CH3:21].Cl>C1(C)C=CC=CC=1>[CH2:20]([CH:7]1[CH2:8][C:3](=[O:1])[CH:4]=[CH:5][N:6]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 692784-MethoxypyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 53419195benzyl 2-ethyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylateYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 4-methoxylpyridine 81 (4.41 g, 40.5 mmol) in toluene (200 mL) at −20° C. was added CbzCl (5.7 ml, 40.5 mmol) in toluene (200 mL) dropwise. After 15 min, ethylmagnesium bromide (23 mL, 2M in THF, 46 mmol) was added dropwise. After 1 hr, 10% aqueous HCl (100 mL) was added and the mixture stirred overnight. The mixture was separated and the organic layer was washed with sat. NaHCO3 and brine. It was dried and concentrated to afford 82 (9 g, 36.4 mmol, 89.9%) that was used directly in the next reaction.

Workup

  1. waitAfter 1 hr
  2. customThe mixture was separated
  3. washthe organic layer was washed with sat. NaHCO3 and brine
  4. customIt was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5516529a5feb4309858df49e05ee3ecc
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Linked notes

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