Benzyl Bromide → Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylate

HRID 868156Notes

Reaction equation

HRID 868156 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][O:14][C:15]2[C:16](=[O:24])[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[NH:19][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[C:26]1([CH2:25][O:24][C:16]2[C:15]([O:14][CH2:13][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:20][N:19]=[C:18]([C:21]([O:23][CH2:13][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:22])[CH:17]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Product 1

HCID 14182499Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21.5 g (156 mmol) of potassium carbonate was added to a suspension of 29.4 g (120 mmol) of 1,4-dihydro-5-(phenylmethoxy)-4-oxo-2-pyridinecarboxylic acid in 350 ml of N,N-dimethylformamide (DMF) and stirred for 1 hour at room temperature. 31 ml (264 mmol) of benzylbromide was added and the mixture was heated at 100° C. under stirring for 25 hours. After cooling to room temperature, the DMF was distilled off in vacuo and the residue triturated with ethyl acetate with short heating to 60° C. 40 g of inorganic salts were filtered off, the filtrate was concentrated to ca. 75 ml and chromatographed on silica gel with ethyl acetate:petroleum ether 90:10 as eluent. Yield: 35.5 g; melting point 116.7° C.

Workup

  1. temperaturethe mixture was heated at 100° C.
  2. stirringunder stirring for 25 hours
  3. temperatureAfter cooling to room temperature
  4. distillationthe DMF was distilled off in vacuo
  5. customthe residue triturated with ethyl acetate
  6. temperaturewith short heating to 60° C
  7. filtration40 g of inorganic salts were filtered off
  8. concentrationthe filtrate was concentrated to ca. 75 ml
  9. customchromatographed on silica gel with ethyl acetate:petroleum ether 90:10 as eluent

Sources & evidence

ORD record
ord-e0cabc26e6b34a69a3fe33fe8ceca689
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

Loading…