Thionyl Chloride → HCID 19706759, compound

HRID 726636Notes

Reaction equation

HRID 726636 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH3:15])[C:7]([CH2:16]O)=[CH:6]2.S(Cl)([Cl:20])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH3:15])[C:7]([CH2:16][Cl:20])=[CH:6]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19706721HCID 19706721, compound

Product 1

HCID 19706759HCID 19706759, compound

Procedure

6,7-Dimethoxy-2-methylquinoline-3-methanol (2.31 g, 9.9 mmol) was dissolved in thionylchloride (50 ml) and refluxed for 2 h. The solution was concentrated and the residue partitioned between ethyl acetate and aqeous NaHCO3. The layers were separated and the aqeous phase extracted with ethyl acetate. The combined organic phases were washed with water and brine and dried over MgSO4. Evaporation of the solvent gave 2.48 g 6,7-dimethoxy-3-chloromethyl-2-methylquinoline.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe solution was concentrated
  3. customthe residue partitioned between ethyl acetate and aqeous NaHCO3
  4. customThe layers were separated
  5. extractionthe aqeous phase extracted with ethyl acetate
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-07cd0f319cb14ff9969f3f08d997c55c
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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