m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1819463ノート

反応式

HRID 1819463 の反応式
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22]O)=[O:21]>CCO>[CH:13]1[CH:12]=[N+:11]([O-:21])[CH:10]=[C:9]([CH2:8][NH2:7])[CH:14]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([OH:22])=[O:21]

参加物

5

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamate

生成物 2

HCID 4473-Chlorobenzoic AcidHCID 2985103-Aminomethylpyridine-N-oxide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

To pyridin-3-ylmethyl-carbamic acid tert-butyl ester (3.89 g, 18.7 mmol) dissolved in EtOH (50 mL), was added 3-chloroperoxybenzoic acid (4.7 g, 27.4 mmol). After 4 hours the volatiles were removed in vacuo and the crude was redissolved in CH2Cl2 (25 mL). To this solution was added TFA (25 mL) and the reaction was stirred at 25° C. for 2 h then the volatiles were removed in vacuo. The crude was redissolved in CH2Cl2 and evaporated. This procedure was done twice more. (1-Oxy-pyridin-3-yl)-methylamine was obtained with contamination of 3-chlorobenzoic acid, but carried further without any additional purification (2.74 g).

後処理

  1. customAfter 4 hours the volatiles were removed in vacuo
  2. dissolutionthe crude was redissolved in CH2Cl2 (25 mL)
  3. additionTo this solution was added TFA (25 mL)
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe crude was redissolved in CH2Cl2
  6. customevaporated

出典と根拠

ORDレコード
ord-aeff01c2c8bf433d8d1819f7576bf421
出典データセット
uspto-grants-2009_10
特許番号
US07601714B2

反応ノート

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