Hydrochloric Acid → 4-[(3-Phenylprop-2-en-1-yl)amino]benzoic acid

HRID 1703087Notes

Reaction equation

HRID 1703087 reaction equation
[CH2:1]([NH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[K+].C(O)C.O.Cl>O>[CH2:1]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:20][CH:21]=1)[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 53948325Ethyl 4-[(3-phenylprop-2-en-1-yl)amino]benzoate

Product 1

HCID 545371064-[(3-Phenylprop-2-en-1-yl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g. of ethyl p-(cinnamylamino)benzoate (prepared as described in Example 24), 10 g. of potassium hydroxide and 200 ml. of ethanol-water (9:1) is refluxed for 3 hours. The solution is acidified while hot with concentrated hydrochloric acid, diluted with water, cooled and filtered to give off-white crystals. Recrystallization from ethanol gives pale yellow crystals, m.p. 200°-202° C.

Workup

  1. additionA mixture of 10 g
  2. temperaturecooled
  3. filtrationfiltered
  4. customto give off-white crystals
  5. customRecrystallization from ethanol
  6. customgives pale yellow crystals, m.p. 200°-202° C.

Sources & evidence

ORD record
ord-d6dda8e022394d429dfc6664585108b7
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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