Methanol → HCID 86685992, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[N:17][CH:18]=1)[CH2:6][CH2:5]2.S(Cl)(Cl)=O.[CH3:27]O>>[CH3:27][O:21][C:20](=[O:22])[CH2:19][C:15]1[CH:16]=[N:17][CH:18]=[C:13]([N:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[C:8]2=[O:12])[CH:14]=1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of [5-(6-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-3-yl]-acetic acid (example 263 [B]) (217 mg, 0.68 mmol) in methanol (25 mL) was added thionyl chloride (0.44 mL, 6.0 mmol) slowly at 0° C. After the addition, the reaction mixture was warmed up and heated at 80° C. for 2 hours. After cooling back to room temperature, it was concentrated in vacuo and the residue was dissolved in EtOAc (150 mL) and washed with satd. aq. NaHCO3 solution and then brine. The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (224 mg, quant.) as light brown oil. MS: 331.1 (M+H+).