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

HRID 1290167Notes

Reaction equation

HRID 1290167 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-af329abe7e2f445ba79cfc209a513b35
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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