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

HRID 638074Notes

Reaction equation

HRID 638074 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-e95bdf643b8944439432b373f3b6c612
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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