Hydrochloric Acid → Methyl 4-chloroanthranilate

HRID 1672179Notes

Reaction equation

HRID 1672179 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-bc116d57e6c94725923e8fcf2f53eefc
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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