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

HRID 917550Notes

Reaction equation

HRID 917550 reaction equation
[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]

Participants

3

Reactant 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamide

Product 1

HCID 552646173-Chloro-5-(hydroxymethyl)benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3468c7ebc07e4c319a4544d9e81e1982
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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