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

HRID 2422534노트

반응식

HRID 2422534 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-57f35f98304848da932abdacb368ea8d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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