Hydrochloric Acid → Methyl 2-amino-5-chlorobenzoate

HRID 236620Notes

Reaction equation

HRID 236620 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:13](=O)([O-])[O-].[Na+].[Na+]>CO.O>[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([Cl:1])=[CH:8][C:4]=1[C:5]([O:7][CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 78878Methyl 2-amino-5-chlorobenzoateYield 57.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of hydrogen chloride (27.1 g) in methanol (192.2 g) is stirred at room temperature and 2-amino-4-chlorobenzoic acid (25 g) is added. The mixture is heated under reflux for 10 hours, then cooled and neutralised with a solution of sodium carbonate (20 g) in water (200 ml). The solid is filtered off, washed with water, and dried in vacuo at 65° C. to give methyl 2-amino-5-chlorobenzoate (15.5 g).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 10 hours
  3. temperaturecooled
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customdried in vacuo at 65° C.

Sources & evidence

ORD record
ord-feef69200ce947deb4605e8d75cc6675
Source dataset
uspto-grants-1987_02
Patent number
US04645818

Reaction notes

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