Chloroform → HCID 68693148, compound

HRID 1296295Notes

Reaction equation

HRID 1296295 reaction equation
O[CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]1[CH:14]([CH3:17])CO.S(Cl)([Cl:20])=O.[CH:22]([Cl:25])(Cl)Cl>>[Cl:20][CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]1[CH:14]([CH3:17])[CH2:22][Cl:25]

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 24386Thionyl ChlorideHCID 68690078HCID 68690078, compound

Product 1

HCID 68693148HCID 68693148, compoundYield 69%

Procedure

3-(Hydroxymethyl)-2-(1-hydroxypropan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (from Isomer B, 0.20 g, 0.85 mmol) in chloroform (7.6 ml) was added to a stirring solution of thionyl chloride (1.8 ml) in chloroform (10 ml). After refluxing overnight the condenser was removed and the majority of the solvent allowed to evaporate over the next 4 h. The residue was purified by flash chromatography (SiO2, CH2Cl2 to 50% EtOAc in CH2Cl2) affording pure product (0.16 g, 69% yield). MS (ESI) 273/275 (M+H).

Workup

  1. temperatureAfter refluxing overnight the condenser
  2. customwas removed
  3. customto evaporate over the next 4 h
  4. customThe residue was purified by flash chromatography (SiO2, CH2Cl2 to 50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-d3eda4e0b1fa45829d935b9536234a2e
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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