4-Aminobenzoic Acid → 4-((Ethoxycarbonyl)amino)benzoic acid

HRID 580461Notes

Reaction equation

HRID 580461 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.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:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10928Ethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 6105984-((Ethoxycarbonyl)amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A mixture composed of 4-aminobenzoic acid (10 g), 1N aqueous sodium bicarbonate solution (365 cc) and ethyl chloroformate (7 cc) is left stirring for 30 minutes at 5° C. 2.5N hydrochloric acid (150 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). 4-(Ethoxycarbonylamino)benzoic acid (13.8 g), m.p. 207° C., is 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-eb0c8ab7bbf14c9f8cba2a832c5e7c15
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

Loading…