Methanol → HCID 86685992, compound

HRID 2277698Notes

Reaction equation

HRID 2277698 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]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86685988HCID 86685988, compound

Product 1

HCID 86685992HCID 86685992, compound

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+).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed up
  3. temperatureAfter cooling back to room temperature
  4. concentrationit was concentrated in vacuo
  5. dissolutionthe residue was dissolved in EtOAc (150 mL)
  6. washwashed with satd
  7. customThe organic layer was dried over anhy
  8. filtrationNa2SO4, filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acb0750dd61a406b9345acfdef9e8dc9
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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