Thionyl Chloride → 4-Chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline

HRID 463715Notes

Reaction equation

HRID 463715 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])[C:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[N:8][CH:7]=[C:6]2[CH2:26]O.S(Cl)([Cl:30])=O>C(Cl)Cl>[Cl:30][CH2:26][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135605346,7-Dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline methanol

Product 1

HCID 135605294-Chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cold mixture of 26.8 g of 6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline methanol in 600 ml of methylene chloride was treated dropwise with 27 ml of thionyl chloride over 15 minutes. The cooling bath was removed and the solution was allowed to stir at ambient temperature for 3 hours after which the volatiles were removed in vacuo. The residue was mixed with methylene chloride and water followed by careful addition of excess sodium bicarbonate. The organic layer was separated, dried over sodium sulfate, evaporated, and crystallized from ethyl acetate to give 23.1 g of 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline as a yellow solid, mp 153° dec. Recrystallization from ethyl acetate provided the analytically pure material, mp 153° dec.

Workup

  1. customThe cooling bath was removed
  2. customwere removed in vacuo
  3. additionThe residue was mixed with methylene chloride and water
  4. additionfollowed by careful addition of excess sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c4baf1221dc84f52b6c9af2bd9a1d00e
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

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