Hydrochloric Acid → 4-{[2-(Thiophen-2-yl)ethyl]amino}benzoic acid

HRID 1389778Notes

Reaction equation

HRID 1389778 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1.[OH-].[K+].C(O)C.Cl>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 13079686Ethyl 4-{[2-(thiophen-2-yl)ethyl]amino}benzoate

Product 1

HCID 130796854-{[2-(Thiophen-2-yl)ethyl]amino}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 29.7 g. of crude ethyl 4-[2-(2-thienyl)-ethylamino]benzoate, 20 g. of potassium hydroxide and 200 ml. of 95% ethanol is refluxed for 3 hours. The solution is diluted with 100 ml. of water and adjusted to pH 6 with concentrated hydrochloric acid. The mixture is cooled, filtered and the solid washed with ethanol-water (1:1) to give a solid. The solid is heated with 200 ml. of ethanol, filtered and the filtrate concentrated. Purification gives the product, m.p. 163°-165° C.

Workup

  1. additionA mixture of 29.7 g
  2. additionThe solution is diluted with 100 ml
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washthe solid washed with ethanol-water (1:1)
  6. customto give a solid
  7. temperatureThe solid is heated with 200 ml
  8. filtrationof ethanol, filtered
  9. concentrationthe filtrate concentrated
  10. customPurification
  11. customgives the product, m.p. 163°-165° C.

Sources & evidence

ORD record
ord-22224544fe974fe995bea7845cb836c3
Source dataset
uspto-grants-1981_01
Patent number
US04246275

Reaction notes

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