Hydrochloric Acid → Methyl 4-aminobenzoate

HRID 1676851Notes

Reaction equation

HRID 1676851 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12]O>>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9784-Aminobenzoic Acid

Product 1

HCID 12082Methyl 4-aminobenzoate

Procedure

To a solution of 4-amino benzoic acid (100 grams, 729.18 mmol) in methanol (1000 mL) at 0° C. is passed dry HCl for 3 hours. The solution is then refluxed for 10 hours. Excess methanol is distilled, and water (1000 mL) is added. The solution is neutralized with dilute ammonia, filtered, and purified from an appropriate solvent.

Workup

  1. customat 0° C.
  2. customfor 3 hours
  3. temperatureThe solution is then refluxed for 10 hours
  4. distillationExcess methanol is distilled
  5. additionwater (1000 mL) is added
  6. filtrationfiltered
  7. custompurified from an appropriate solvent

Sources & evidence

ORD record
ord-c9eeda1c72a5415e91722b3bee296480
Source dataset
uspto-grants-2011_08
Patent number
US08007526B2

Reaction notes

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