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

HRID 1089467Notes

Reaction equation

HRID 1089467 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 sitrred 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. concentrationconcentrated
  7. additionThe residue was treated with chloroform and water
  8. customthe chloroform layer was collected
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customthe residue was recrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-41560439acc74a15b93e0c2f381a130a
Source dataset
uspto-grants-1990_10
Patent number
US04966904

Reaction notes

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