3-Chloro-5-(hydroxymethyl)benzamide → 3-Chloro-5-(hydroxymethyl)benzylamine

HRID 917550ノート

反応式

HRID 917550 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][OH:12])[CH:10]=1)[C:5]([NH2:7])=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][OH:12])[CH:10]=1)[CH2:5][NH2:7]

参加物

3

反応物 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamide

生成物 1

HCID 552646173-Chloro-5-(hydroxymethyl)benzylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Step N5. To 3-chloro-5-(hydroxymethyl)benzamide (0.7 g, 3.77 mmol) in THF (20 mL) was added borane-dimethylsulfide complex (0.9 g, 11.8 mmol) slowly. The mixture was refluxed for 20 hours. Excess borane reagent was quenched with methanol and solvent was removed by rotovap. The resulting residue was purified by column with dichloromethane/methanol (1:1) as the eluant. 3-chloro-5-(hydroxymethyl)benzylamine was obtained in white solid (240 mg, 37%). 1H NMR (300 MHz, CD3OD): δ 3.81 (s, 2H), 4.61 (s, 2H), 7.25 (s, 1H), 7.28 (s, 1H), 7.59, 7.30 (s, 1H). MH+=172.08.

後処理

  1. temperatureThe mixture was refluxed for 20 hours
  2. customExcess borane reagent was quenched with methanol and solvent
  3. customwas removed by rotovap
  4. customThe resulting residue was purified by column with dichloromethane/methanol (1:1) as the eluant

出典と根拠

ORDレコード
ord-3468c7ebc07e4c319a4544d9e81e1982
出典データセット
uspto-grants-2007_09
特許番号
US07273882B2

反応ノート

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