Thionyl Chloride → 7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 2388134Notes

Reaction equation

HRID 2388134 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:10](CC2C=CC(OC)=CC=2OC)[CH2:9][C:8]2[N:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:24][C:7]=2[C:6]1=[O:31])=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]2[N:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:24][C:7]=2[C:6]=1[OH:31])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 675309395-(2,4-Dimethoxy-benzyl)-7-oxo-2-phenyl-4,5,6,7-tetrahydro-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 675295697-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl esterYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2,4-Dimethoxy-benzyl)-7-oxo-2-phenyl-4,5,6,7-tetrahydro-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (1.05 g, 2.49 mmol), was dissolved in 17 mL of anhydrous dichloromethane. To the solution was added 272 μL of thionyl chloride, and the reaction was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 0.20 g of the title compound as a white solid. MS: (−) m/z 269.1 (M−1).

Workup

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f16c3a6f0b104bd0b8d1dd95c3f8197b
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…