Acetic Acid → HCID 135458202, compound

HRID 2053414Notes

Reaction equation

HRID 2053414 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH2:18][OH:19])[CH:14]=1)=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(O)=[O:28]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([C:18]([OH:28])=[O:19])[CH:14]=1)=[C:5]2[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 135545395HCID 135545395, compound

Product 1

HCID 135458202HCID 135458202, compoundYield 21%

Conditions

Temperature
50 °C

Procedure

To a solution of 6-chloro-3-(3-hydroxymethyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (example 21) (353 mg, 1 mmol) in HOAc (1 mL), CrO3 (100 mg, 1 mmol) was added. The resulting mixture was stirred at 50° C. for 3 h. The reaction mixture was allowed to cool to RT and HOAc was removed. The residue was subjected to reversed phase HPLC to obtain the title compound. Yield 21%.

Workup

  1. temperatureto cool to RT
  2. customHOAc was removed

Sources & evidence

ORD record
ord-33709e0fad4040b5a3469dcb15cfd64d
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

Loading…