2-Amino-4-chlorobenzoic acid → Methyl 4-chloroanthranilate

HRID 1605157Notes

Reaction equation

HRID 1605157 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.[CH3:13]O>>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH3:13])=[O:7]

Participants

3

Reactant 2

HCID 666462-Amino-4-chlorobenzoic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 80001Methyl 4-chloroanthranilate

Procedure

The starting material is prepared as follows: Through the suspension of 500 g of 4-chloroanthranilic acid in 3 lt of methanol hydrogen chloride is bubbled for 2 hours while cooling with ice and the mixture refluxed for 10 hours under hydrogen chloride. It is cooled to room temperature, filtered, the filtrate evaporated and the combined residues partitioned between 3 lt of diethyl ether and 4.5 lt of water, the pH of which is adjusted to 10 with 10% aqueous sodium hydroxide. The aqueous layer is extracted 3 times with 2.25 lt of diethyl ether, the combined extracts washed with water, dried, filtered and evaporated, to yield the methyl 4-chloroanthranilate melting at 58°-60°.

Workup

  1. customThe starting material is prepared
  2. customis bubbled for 2 hours
  3. temperaturewhile cooling with ice
  4. temperaturethe mixture refluxed for 10 hours under hydrogen chloride
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customthe combined residues partitioned between 3 lt of diethyl ether and 4.5 lt of water
  8. extractionThe aqueous layer is extracted 3 times with 2.25 lt of diethyl ether
  9. washthe combined extracts washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-60c42e9e582c485abc354cd9e5eed6d2
Source dataset
uspto-grants-1976_04
Patent number
US03949081

Reaction notes

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