3-Nitrobenzaldehyde → alpha-[(3-Nitrobenzylamino)methyl]-3,4-dimethoxybenzyl alcohol

HRID 2352246Notes

Reaction equation

HRID 2352246 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].Cl.[NH2:13][CH2:14][CH:15]([OH:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1.[BH4-].[Na+]>CO.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH:13][CH2:14][CH:15]([OH:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochloride

Product 1

HCID 14719589alpha-[(3-Nitrobenzylamino)methyl]-3,4-dimethoxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

m-Nitrobenzaldehyde (1.8 g) was added to a suspension of α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride in 25 ml methanol, triethylamine (2.8 ml) was further added dropwise at room temperature with stirring, and the resulting solution was heated under reflux for 30 minutes. After cooling, sodium borohydride (1.45 g) was added in small portions with stirring under ice cooling, and the mixture was stirred at room temperature for one hour and concentrated. The residue was treated with chloroform and water, and the chloroform layer was collected, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ether/n-hexane, affording 3.3 g of pure α-[(3-nitrobenzylamino)methyl]-3,4-dimethoxybenzyl alcohol, m.p. 105°-107° C.

Workup

  1. additionwas further added dropwise at room temperature
  2. temperaturethe resulting solution was heated
  3. temperatureunder reflux for 30 minutes
  4. temperatureAfter cooling
  5. stirringwith stirring under ice cooling
  6. stirringthe mixture was stirred at room temperature for one hour
  7. concentrationconcentrated
  8. additionThe residue was treated with chloroform and water
  9. customthe chloroform layer was collected
  10. washwashed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe solvent was distilled off
  13. customthe residue was recrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-ef775a0da7554420a68b48782eb0fe42
Source dataset
uspto-grants-1989_10
Patent number
US04876261

Reaction notes

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