m-Chloroperbenzoic acid → HCID 13560531, compound

HRID 638080Notes

Reaction equation

HRID 638080 reaction equation
[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[N:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[N+:5]([O-:36])[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 135605294-Chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline

Product 1

HCID 13560531HCID 13560531, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 5.2 g 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl) methyl] isoquinoline in 150 ml methylene chloride, was added under stirring and nitrogen a solution of 3.04 g m-chloroperbenzoic acid in 100 ml methylene chloride over 2 hours, so that the temperature did not exceed 3°-5°. The solution was stirred over night at room temperature and the red solution applied to a column, packed with 100 g silica gel 60 Merck, 230-400 mesh ASTM. From elution with ether and ethyl acetate the unreacted base 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline was separated. Elution with ethyl acetate/ethanol (4:1) afforded 3.8 g of a brownish foam. The 4-(chloromethyl)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline 2oxide crystallized from methylene chloride/ethyl acetate: 3.5 g yellow crystals, mp 167°-168°.

Workup

  1. additionwas added
  2. customdid not exceed 3°-5°
  3. stirringThe solution was stirred over night at room temperature
  4. washFrom elution with ether and ethyl acetate the unreacted base 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline
  5. customwas separated
  6. washElution with ethyl acetate/ethanol (4:1)

Sources & evidence

ORD record
ord-83411940463d45639507044041d4c698
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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