7-Methylquinoline → 7-Methylquinoline 1-oxide

HRID 2422532Notes

Reaction equation

HRID 2422532 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:17].[OH-].[Ca+2].[OH-]>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 119277-MethylquinolineHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium Hydroxide

Product 1

HCID 232711687-Methylquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methylquinoline (20.0 g, 140 mmol) in dichloromethane (700 mL) was added 3-chloroperoxybenzoic acid (50%, 62.6 g, 182 mmol) and stirred at room temperature for 2 h. Solid calcium hydroxide (13.4 g, 182 mmol) was added and 15 min later the mixture was filtered through celite, rinsed with dichloromethane and the liquors evaporated to dryness to give the title compound. The compound was used as such for the next step. 1H NMR (400 MHz, acetone-d6): δ 8.45 (m, 2H), 7.93 (d, 1H), 7.80 (d, 1H), 7.55 (d, 1H), 7.35 (m, 1H), 2.60 (s, 3H).

Workup

  1. filtrationwas filtered through celite
  2. washrinsed with dichloromethane
  3. customthe liquors evaporated to dryness

Sources & evidence

ORD record
ord-470f6f82cc824c1eb77f8868ae841afa
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…