Hydrochloric Acid → Methyl 4-chloroanthranilate

HRID 1892166Notes

Reaction equation

HRID 1892166 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 80001Methyl 4-chloroanthranilateYield 62%

Procedure

To a mixture of 2-amino-4-chlorobenzoic acid (150 g, 0.88 mol) in MeOH (2.6 L) was added conc. HCl (0.5 L, 16.5 mol) and the reaction mixture was allowed to stir at reflux. After 12 h, the reaction mixture was allowed to cool to rt and was concentrated. Water (0.5 L) was added to the residue and the solution basified with 10% aqueous NaOH. The resulting precipitate was filtered to give methyl 2-amino-4-chlorobenzoate (101 g, 62%).

Workup

  1. temperatureat reflux
  2. concentrationwas concentrated
  3. additionWater (0.5 L) was added to the residue
  4. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-875a189518e04c119ea6f67d7cd9f975
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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