Thionyl Chloride → HCID 86685969, compound

HRID 2277675Notes

Reaction equation

HRID 2277675 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH2:23]O)[CH:22]=1)[CH2:10][CH2:9]2>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH2:23][Cl:3])[CH:22]=1)[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86685959HCID 86685959, compound

Product 1

HCID 86685969HCID 86685969, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3.5 °C

Procedure

Thionyl chloride (1.4 mL, 19.0 mmol) was added slowly at 0° C. to a solution of 6-chloro-2-(5-hydroxymethyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (example 3 [B]) (1.1 g, 3.8 mmol) in DCM (50 mL). After the addition, the reaction mixture was stirred at 2-5° C. for 2 hours before it was poured into satd. aq. NaHCO3 solution (50 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (1.42 g, 92%) as light yellowish solid. MS: 307.0 & 309.0 (M+H+).

Workup

  1. additionAfter the addition
  2. additionwas poured into satd
  3. extractionaq. NaHCO3 solution (50 mL) and extracted with EtOAc (2×150 mL)
  4. washThe organic layer was washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2a4f84f70244d3e91b8872f383e77e0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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