m-Chloroperbenzoic acid → 7-Methylquinoline-2-carbonitrile 1-oxide

HRID 2422534Notes

Reaction equation

HRID 2422534 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].[OH-].[Ca+2].[OH-]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N+:9]([O-:19])[C:8]([C:12]#[N:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 107971837-Methylquinoline-2-carbonitrile

Product 1

HCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methylquinoline-2-carbonitrile (14.2 g, 84 mmol) in dichloromethane (400 mL) was added 3-chloroperoxybenzoic acid (50%, 36.4 g, 106 mmol) and stirred at room temperature overnight. Solid calcium hydroxide (7.8 g, 106 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 crude compound. The compound was purified by flash chromatography on silica gel (eluting with 5% acetone in dichloromethane) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.40 (s, 1H), 8.05 (d, 1H), 7.97 (d, 1H), 7.75 (m, 2H), 2.65 (s, 3H).

Workup

  1. filtrationwas filtered through celite
  2. washrinsed with dichloromethane
  3. customthe liquors evaporated to dryness
  4. customto give the crude compound
  5. customThe compound was purified by flash chromatography on silica gel (eluting with 5% acetone in dichloromethane)

Sources & evidence

ORD record
ord-57f35f98304848da932abdacb368ea8d
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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