Water → N-(4-hydroxymethyl-2-nitrophenylmethyl)acetamide

HRID 1282067Notes

Reaction equation

HRID 1282067 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2].[BH4-].[Li+].O>O1CCCC1>[OH:11][CH2:10][C:9]1[CH:14]=[CH:15][C:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 18423167Methyl 4-acetamidomethyl-3-nitrobenzoate

Product 1

HCID 18423007N-(4-hydroxymethyl-2-nitrophenylmethyl)acetamideYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-acetamidomethyl-3-nitrobenzoate (20 g) and lithium borohydride (1.7 g) in tetrahydrofuran (200 ml) was stirred at 40-50° C. for 2.5 hr. The reaction mixture was poured into water (150 ml) and extracted with ethylacetate (100 ml×3). The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow oil (15.5 g). The obtained yellow oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give a pale-brown solid (13.5 g). The obtained solid was crystallized from ethyl acetate/ethanol/hexane (30:2:5) to give the title compound (12 g) as yellow white crystals.

Workup

  1. extractionextracted with ethylacetate (100 ml×3)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4ff8a57551f147d7bd0b9bc32e805e8f
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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