Water → 4-Amino-2-ethoxy-5-nitrobenzoic acid

HRID 345538Notes

Reaction equation

HRID 345538 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:15][CH2:16][CH3:17])[CH:3]=1.[OH-].[Na+].O>C(O)(=O)C>[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:15][CH2:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15096751Methyl 4-amino-2-ethoxy-5-nitrobenzoate

Product 1

HCID 198834474-Amino-2-ethoxy-5-nitrobenzoic acidYield 66.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.8 parts of methyl 4-amino-2-ethoxy-5-nitrobenzoate, 1.6 parts of sodium hydroxide and 30 parts of water was stirred and refluxed for 30 minutes. The reaction mixture was cooled and 50 parts of water were added. The whole was neutralized by the dropwise addition of glacial acetic acid. The precipitated product was filtered off and crystallized from 2-propanol at 0° C. The product was filtered off, washed with a small amount of 2,2'-oxybispropane and dried, yielding 3 parts (66.6%) of 4-amino-2-ethoxy-5-nitrobenzoic acid; mp. 230° C. (intermediate 34).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitated product was filtered off
  4. customcrystallized from 2-propanol at 0° C
  5. filtrationThe product was filtered off
  6. washwashed with a small amount of 2,2'-oxybispropane
  7. customdried

Sources & evidence

ORD record
ord-29d074dfa68f4dd4b76c831333fe01a3
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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