Nitric Acid → Methyl 4-acetamidomethyl-3-nitrobenzoate

HRID 1282066Notes

Reaction equation

HRID 1282066 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]([NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)(=[O:12])[CH3:11]>>[C:10]([NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[N+:1]([O-:4])=[O:2])(=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 15550681Methyl 4-(acetamidomethyl)benzoate

Product 1

HCID 18423167Methyl 4-acetamidomethyl-3-nitrobenzoate

Procedure

To a mixture (mixed acid) of fuming nitric acid (70 ml) and conc. sulfuric acid (70 ml) was added methyl 4-acetamidomethylbenzoate (54 g) at 7-15° C. for 1.5 hr. This reaction mixture was stirred at room temperature for 1 hr and poured into ice water (600 ml). The mixture was extracted with chloroform (300 ml×3). The extract was washed with water, saturated sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow oil (75 g). The obtained yellow oil was crystallized from ethyl acetate (50 ml) and recrystallized from hexane/ethyl acetate (1:1, 600 ml) to give the title compound (45.5 g) as pale-yellow crystals.

Workup

  1. extractionThe mixture was extracted with chloroform (300 ml×3)
  2. washThe extract was washed with water, saturated sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4c06ea0421ea4815980b81d172d0235d
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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