Sodium borohydride → 3,5-dichloro-4-hydroxymethyl-N-methylaniline

HRID 1899985Notes

Reaction equation

HRID 1899985 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[CH:10]=[O:11])[NH:5][CH3:6].[BH4-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:12])[C:9]=1[CH2:10][OH:11])[NH:5][CH3:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18923365HCID 18923365, compound

Product 1

HCID 189235483,5-dichloro-4-hydroxymethyl-N-methylanilineYield 100.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dichloro-4-formyl-N-methylaniline (242 mg) in methanol (3 ml) and tetrahydrofuran (3 ml) was added sodium borohydride (45 mg) and the mixture was stirred for 30 minutes at ambient temperature. The reaction mixture was quenched with aqueous saturated ammonium chloride solution and ethyl acetate was added thereto. The separated organic layer was washed with aqueous saturated ammonium chloride solution, dried and concentrated in vacuo to give 3,5-dichloro-4-hydroxymethyl-N-methylaniline (246 mg).

Workup

  1. customThe reaction mixture was quenched with aqueous saturated ammonium chloride solution and ethyl acetate
  2. additionwas added
  3. washThe separated organic layer was washed with aqueous saturated ammonium chloride solution
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8dfb09752d14245ace2dc75f4a9f130
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

Loading…