Sulfuric Acid → Methyl 5-amino-2-ethoxy-4-nitrobenzoate

HRID 1789072Notes

Reaction equation

HRID 1789072 reaction equation
C([NH:4][C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13]C)=[O:11])(=O)C.S(=O)(=O)(O)O>>[NH2:4][C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 13912858Ethyl 5-acetamido-2-ethoxy-4-nitrobenzoate

Product 1

HCID 13912859Methyl 5-amino-2-ethoxy-4-nitrobenzoate

Procedure

A suspension of 1 5 g of ethyl 5-acetylamino-2-ethoxy-4-nitrobenzoate in 50 ml of 5 % (v/v) sulfuric acid methanolic solution was refluxed for 4 hours After cooling, the reaction solution was poured into an ice water, the resulting crystals were collected by filtration and recrystallized from methanol to give the title compound, m.p. 156°-157° C., yield of 1.01 g.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4f322b0df7884eecbb913acbcc3a95a3
Source dataset
uspto-grants-1987_08
Patent number
US04686292

Reaction notes

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