m-Chloroperbenzoic acid → HCID 21679660, compound

HRID 1948252Notes

Reaction equation

HRID 1948252 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2>C(Cl)Cl.CO>[Cl:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N+:17]([O-:9])=[CH:18]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2249335-chloroisoquinoline

Product 1

HCID 21679660HCID 21679660, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

According to Scheme 28 Step 1: A solution of MCPBA (1.9, 15.0 mmol, 3.6 g) and 5-chloroisoquinoline (1 eq, 7.80 mmol, 1.27 g) in CH2Cl2 (30 mL) was stirred for 2 hours at room temperature. The reaction mixture was diluted with CH2Cl2 (20 mL) and MeOH (10 mL) and the organic phase washed with 2M NaOH solution. The aqueous layer was extracted with CH2Cl2. The organic fractions were combined, dried over MgSO4, filtered and evaporated to yield the title compound (6.20 mmol, 1.12 g, 79%) as an orange solid.

Workup

  1. washthe organic phase washed with 2M NaOH solution
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d3dbdc93a4c7418d823cfa593e9488f0
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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