Hydrochloric Acid → Methyl 4-chloroanthranilate

HRID 2387968Notes

Reaction equation

HRID 2387968 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-873aeeb0a80f400bb408bbf78edf57ad
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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