m-Chloroperbenzoic acid → HCID 21088914, compound

HRID 350662Notes

Reaction equation

HRID 350662 reaction equation
[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:13])[N:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:13])[N+:4]=1[O-:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13681372HCID 13681372, compound

Product 1

HCID 21088914HCID 21088914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 300 mg of 1-chloromethyl-3-methyl-isoquinoline in 3 ml of methylene chloride is combined with 390 mg of 3-chloroperoxybenzoic acid and stirred overnight at ambient temperature. The reaction mixture is diluted with some methylene chloride and extracted with saturated sodium hydrogen carbonate solution. The combined organic phases are dried over magnesium sulphate and evaporated down. The solid, yellowish crude product is triturated with tert.-butylmethylether, suction filtered, washed with tert.-butylmethylether and dried.

Workup

  1. extractionextracted with saturated sodium hydrogen carbonate solution
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customevaporated down
  4. customThe solid, yellowish crude product is triturated with tert.-butylmethylether, suction
  5. filtrationfiltered
  6. washwashed with tert.-butylmethylether
  7. customdried

Sources & evidence

ORD record
ord-85a751e6f4dd4ce391463003e52e8d36
Source dataset
uspto-grants-2007_02
Patent number
US07183280B2

Reaction notes

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