m-Chloroperbenzoic acid → 7-benzyloxyisoquinoline N-oxide

HRID 1067231Notes

Reaction equation

HRID 1067231 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][N:15]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][N+:15]([O-:27])=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 211924457-(Benzyloxy)isoquinoline

Product 1

HCID 541898737-benzyloxyisoquinoline N-oxideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-benzyloxyisoquinoline (International Patent Application publication no. WO 94/20459) (0.50 g, 2.13 mmol) in CH2Cl2 (20 mL) was stirred with 3-chloroperbenzoic acid (mCPBA) (1.1 g, 3.19 mmol) at room temperature for 2.5 h. The mixture was diluted with CH2Cl2, and then washed with sodium dithionite (1 M), potassium carbonate (1 M) and brine. The organic layer was dried over MgSO4 and evaporated in vacuo to leave 7-benzyloxyisoquinoline N-oxide (0.521 g, 2.09 mmol) as a cream-coloured powder.

Workup

  1. washwashed with sodium dithionite (1 M), potassium carbonate (1 M) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-103460cb3b2d4c60a362e33967e8f561
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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