Hydrochloric Acid → 2-Amino-4-(benzyloxy)benzoic acid

HRID 1271212Notes

Reaction equation

HRID 1271212 reaction equation
C([O:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[NH:24]C(=O)C)C1C=CC=CC=1.[OH-].[Na+].Cl>CCO>[NH2:24][C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:10]=1[C:9]([OH:28])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69461669Benzyl 2-acetamido-4-(benzyloxy)benzoate

Product 1

HCID 235458842-Amino-4-(benzyloxy)benzoic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.87 g (4.98 mmol) of 2-acetylamino-4-benzyloxy-benzoic acid benzyl ester in EtOH (20 ml) was treated with 1N NaOH (20–30 ml) and stirred at 95° C.–130° C. (oil bath temperature) until completion of the reaction according to TLC and NMR analysis (reaction time about 34 h). The reaction mixture was cooled to RT, brought to pH 6 on addition of 1N aqueous HCl, the precipitate that formed was filtered off by suction and dried in a high vacuum to give 1.19 g (91.7%) of the desired 2-amino-4-benzyloxy-benzoic acid as an off-white solid. ISP mass spectrum, m/e: 242.2 (M+1 calculated for C14H13NO3: 242).

Workup

  1. customaccording to TLC and NMR analysis (reaction time about 34 h)
  2. customthe precipitate that formed
  3. filtrationwas filtered off by suction
  4. customdried in a high vacuum

Sources & evidence

ORD record
ord-a470bf6560304c04ba726f6a7f75aa29
Source dataset
uspto-grants-2007_04
Patent number
US07205309B2

Reaction notes

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