4-Aminobenzoic Acid → 4-{[(benzyloxy)carbonyl]amino}benzoic acid

HRID 449759Notes

Reaction equation

HRID 449759 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[C:13](Cl)(=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:14][C:13]([NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2201714-{[(benzyloxy)carbonyl]amino}benzoic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Aqueous NaOH (2N, 1.93 g, 48.3 mmol) was added to a solution of 4-aminobenzoic acid (3.0 g, 21.90 mmol) in H2O at 0° C. A clear solution appeared within 5 min. Then, benzyl carbonochloridate (4.45 g, 26.28 mmol) was added dropwise to the mixture and it was heated to room temperature and stirred for 2 h. The reaction mixture was diluted with water and separated with ether. The aqueous layer was cooled to 0° C. temperature and acidified with 6M HCl. The solid was collected by filtration, washed with water and dried. The crude solid was recrystallized from ethyl acetate-hexane to furnish 4-(benzyloxycarbonylamino)benzoic acid 10 (5.0 g, 84%) as a white solid.

Workup

  1. customseparated with ether
  2. temperatureThe aqueous layer was cooled to 0° C. temperature
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe crude solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cf9b66aacb794d6e8797f667cfc8dbab
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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