m-Chloroperbenzoic acid → 5-(Methoxycarbonyl)isoquinoline 2-oxide

HRID 1051240Notes

Reaction equation

HRID 1051240 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:14][O:13][C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N+:2]([O-:23])=[CH:1]2)=[O:12]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 313259Methyl 5-isoquinolinecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 1180908815-(Methoxycarbonyl)isoquinoline 2-oxideYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl isoquinoline-5-carboxylate (5.8 g, 31.0 mmol) obtained in Step (3) above and dichloromethane (60 mL) were mixed and stirred. The reaction solution was added with mCPBA (8.02 g, 46.2 mmol) and stirred for about 5 hours at 50° C. The reaction mixture was cooled to room temperature and adjusted to have a pH value in a range of 9˜10 by adding a saturated aqueous sodium bicarbonate. The reaction mixture was diluted with dichloromethane, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (4 g, 63.5%).

Workup

  1. stirringstirred for about 5 hours at 50° C
  2. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5fa33a11fcc40688ce2ab40e7b7e5cd
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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