Sodium borohydride → N-(5-methyl-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide

HRID 1888950Notes

Reaction equation

HRID 1888950 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](/[N:17]=[CH:18]/[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][CH2:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178492111HCID 178492111, compound

Product 1

HCID 68517409N-(5-methyl-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of compound (E)-N-(5-methyl-2-(3,4,5-trimethoxybenzylideneamino)phenyl)benzamide (3 mmol) in methanol was cooled with an ice bath. Sodium borohydride was added until the color turned white. Excess sodium borohydride was quenched by the addition of distilled water. The resulting mixture was extracted with ethyl acetate (50 mL×3). The combined organics were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuum to obtain N-(5-methyl-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide as a solid.

Workup

  1. temperaturewas cooled with an ice bath
  2. customExcess sodium borohydride was quenched by the addition of distilled water
  3. extractionThe resulting mixture was extracted with ethyl acetate (50 mL×3)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-651f6ba5cbf34505aef966ad6a8c237b
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

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