Hydrochloric Acid → Methyl 5-Amino-2-chlorobenzoate

HRID 1289970Notes

Reaction equation

HRID 1289970 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 378795-Amino-2-chlorobenzoic acid

Product 1

HCID 5200412Methyl 5-Amino-2-chlorobenzoate

Procedure

A solution of 10 g of 2-chloro-5-(amino)benzoic acid in 250 mL of methanol was saturated with HCl (gas) and stirred for 16 h. The solution was concentrated in vacuo, diluted with water, made neutral with 5N NaOH and extracted twice with ether. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated to afford 10 g of title compound as a slightly pink solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted twice with ether
  4. washThe organic layers were washed with a portion of brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-962c7a95dd364b54b228e0e8206131a5
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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