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

HRID 1432065ノート

反応式

HRID 1432065 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-18bfc81a79e64d29ba6d41c9842e1856
出典データセット
uspto-grants-2009_11
特許番号
US07612069B2

反応ノート

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