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

HRID 917550노트

반응식

HRID 917550 반응식
[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]

참가 물질

3

반응물 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamide

생성물 1

HCID 552646173-Chloro-5-(hydroxymethyl)benzylamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3468c7ebc07e4c319a4544d9e81e1982
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273882B2

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