2-Chlorobenzaldehyde → HCID 2168799, compound

HRID 2118515Notes

Reaction equation

HRID 2118515 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 8421HomoveratrylamineHCID 4311764Sodium borohydride

Product 1

HCID 2168799HCID 2168799, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

2-(3,4-Dimethoxyphenyl)-ethylamine (80.3 g, 0.443 mol) and o-chlorobenzaldehyde (62 g, 0.443 mol) are boiled (1 hour) in toluene (500 ml) using a water separator. The reaction mixture is evaporated, the oily residue is taken up in methanol (500 ml) and combined, under vigorous stirring and intensive cooling, with a solution of sodium borohydride (16.9 g, 0.443 mol) in water (50 ml). After it has all been added, the resulting mixture is stirred (1 hour) at ambient temperature, concentrated in vacuo and the residue is distilled in vacuo. Yield: 108.8 g. Bp16.9 Pa : 188°-190° C.

Workup

  1. customThe reaction mixture is evaporated
  2. additionall been added
  3. stirringthe resulting mixture is stirred (1 hour) at ambient temperature
  4. concentrationconcentrated in vacuo
  5. distillationthe residue is distilled in vacuo
  6. custom188°-190° C.

Sources & evidence

ORD record
ord-5c0fb282e78c4daeb1bc958355710590
Source dataset
uspto-grants-1987_07
Patent number
US04678792

Reaction notes

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