m-Chloroperbenzoic acid → 6-Methylisoquinoline-2-oxide

HRID 840110Notes

Reaction equation

HRID 840110 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.ClC1C=CC=C(C(OO)=[O:20])C=1>CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N+:7]([O-:20])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6409596-Methylisoquinoline

Product 1

HCID 216796636-Methylisoquinoline-2-oxideYield 53.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 6-methylisoquinoline (2.0 g, 14 mmol) in ether (80 mL) at 0° C. was added 3-chloroperbenzoic acid (57%, 4.3 g, 14 mmol). The mixture was warmed to room temperature, stirred for 3 h and filtered. The filter-cake was partitioned between chloroform (3×30 mL) and aqueous potassium carbonate solution (30 mL). The combined organic extracts were washed (brine), dried (sodium sulfate) and concentrated in vacuo to give the product as an off-white crystalline solid (1.2 g, 53%): mp 140-142° C.; IR νmax (Nujol)/cm−1 3047, 2925, 2855, 1606, 1562, 1466, 1377, 1328, 1270, 1217, 1182, 1133, 984, 920, 878, 858, 823, 803, 766, 600, 500 and 498; NMR δH (400 MHz, CDCl3) 2.53 (3H, s) 7.47 (1H, d, J 8.5 Hz) 7.59 (1H, d, .J 7.5 Hz) 7.64 (1H, d, J 8.5 Hz) 8.11 (1H, dd, J 2,7.5 Hz) 8.73 (1H, s).

Workup

  1. filtrationfiltered
  2. customThe filter-cake was partitioned between chloroform (3×30 mL) and aqueous potassium carbonate solution (30 mL)
  3. washThe combined organic extracts were washed (brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d18835644721403c988f40813101529c
Source dataset
uspto-grants-2002_04
Patent number
US06365598B1

Reaction notes

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