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

HRID 1432065Notes

Reaction equation

HRID 1432065 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-18bfc81a79e64d29ba6d41c9842e1856
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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