Benzyl Alcohol → 2-Amino-5-chlorobenzoic acid

HRID 1964031Notes

Reaction equation

HRID 1964031 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH:11]C(O)=O)=[CH:4][CH:3]=1.C(O)C1C=CC=CC=1.CN(C=O)C>C(OCC)(=O)C>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 21584726HCID 21584726, compound

Product 1

HCID 124762-Amino-5-chlorobenzoic acidYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (5.1 mmol) of 5-chloroisatoic acid was heated under stirring in a mixed solvent of benzyl alcohol (5 mL) and DMF (5 mL) at 100° C. for 5 hours. After cooling, the reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 0.516 g of 2-amino-5-chlorobenzoic acid.benzylester (yield: 39%).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was separated
  6. custompurified

Sources & evidence

ORD record
ord-ee74b51925a94b6abad65c37346639ab
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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