m-Chloroperbenzoic acid → 4-Chloro-7-methoxy-8-methylquinoline N-oxide

HRID 407543ノート

反応式

HRID 407543 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:22]2[C:17](=[C:18]([CH3:25])[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:22]2[C:17](=[C:18]([CH3:25])[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[N+:16]([O-:9])=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 211019544-Chloro-7-methoxy-8-methylquinoline

生成物 1

HCID 576079424-Chloro-7-methoxy-8-methylquinoline N-oxide収率 18.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Metachloroperbenzoic acid (90.2 g, 366.0 mmol) was added portion wise over 3 h to a solution of 4-chloro-7-methoxy-8-methylquinoline (60, 15.2 g, 73.2 mmol) in CHCl3 (1 L). Then, the solution was partitioned between ice-cooled NaOH 1N and CH2Cl2 (8 successive extractions). The organic layers were combined, dried (Na2SO4) and evaporated. The residue was purified by column chromatography (gradient of AcOEt/CH2Cl2, 1:2 to 1:0) to give 3.0 g (18.3%) of the title product 61 as a pale yellow powder: m/z=224 (M+H)+.

後処理

  1. customThen, the solution was partitioned between ice-
  2. temperaturecooled NaOH 1N and CH2Cl2 (8 successive extractions)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography (gradient of AcOEt/CH2Cl2, 1:2 to 1:0)

出典と根拠

ORDレコード
ord-27363d5fa57448b1a431d637b79c3c10
出典データセット
uspto-grants-2014_06
特許番号
US08754106B2

反応ノート

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