3-Aminobenzoic Acid → 3-[(ethoxycarbonyl)amino]benzoic acid

HRID 580480Notes

Reaction equation

HRID 580480 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)(O)[O-].[Na+].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>Cl>[CH2:20]([O:19][C:17]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 10928Ethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 7176623-[(ethoxycarbonyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A mixture composed of 3-aminobenzoic acid (20 g), 1 M aqueous sodium bicarbonate solution (730 cc) and ethyl chloroformate (14 cc) is left with stirring for 30 minutes at 5° C. 2.5 N hydrochloric acid (300 cc) is then added to the reaction mixture. The precipitate formed is separated by filtration, washed with water (3×200 cc) and dried at 40° C. under reduced pressure (0.07 kPa). 3-Ethoxycarbonylaminobenzoic acid (25 g), m.p. 198° C., is thereby obtained.

Workup

  1. waitis left
  2. customThe precipitate formed
  3. customis separated by filtration
  4. washwashed with water (3×200 cc)
  5. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-1db0a523ae3143fb8a0109927e1b3876
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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