m-Chloroperbenzoic acid → HCID 74539874, compound

HRID 1499098Notes

Reaction equation

HRID 1499098 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[CH:18]=[N:17][CH:16]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1>C(Cl)Cl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[CH:18]=[N+:17]([O-:37])[CH:16]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 74539628HCID 74539628, compound

Product 1

HCID 74539874HCID 74539874, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(dibenzo[b,d]furan-2-ylmethyl)-6,7-dimethoxyisoquinoline 10 (600 mg, 1.62 mmol) in CH2Cl2 (40 mL) was added mCPBA (336 mg, 1.95 mmol) at RT under a nitrogen atmosphere. The reaction mixture was stirred at RT overnight and then this mixture was partitioned between CH2Cl2 (200 mL) and a 1 M K2CO3 aqueous solution (50 mL). The separated organic layer was washed with brine (50 mL), dried over MgSO4, filtered and evaporated to give 4-dibenzofuran-2-ylmethyl-6,7-dimethoxy-isoquinoline 2-oxide 35 (see table 7) as yellow solid (645 mg, quant. yield).

Workup

  1. customthis mixture was partitioned between CH2Cl2 (200 mL)
  2. washThe separated organic layer was washed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-165f2af374434b9cbeaf0ac2f80e68e6
Source dataset
uspto-grants-2015_12
Patent number
US09200016B2

Reaction notes

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