Hydrochloric Acid → 4-Cinnamoylamino-3-methylbenzoic acid

HRID 232702

Reaction equation

HRID 232702 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[CH3:17].[C:18](Cl)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CC(C)=O.O>[C:18]([NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[CH3:17])(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chlorideHCID 755984-Amino-3-methylbenzoic acid

Product 1

HCID 538459644-Cinnamoylamino-3-methylbenzoic acidYield 51.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

8.2 g of potassium carbonate was added to a suspension of 3.0 g of 4-amino-3-methylbenzoic acid in 60 ml of acetone and 60 ml of water. Thereto was dropwise added, with ice-cooling, a solution of 4.0 g of cinnamoyl chloride in 30 ml of acetone. The mixture was stirred at the same temperature for 30 minutes to give rise to a reaction. The reaction mixture was poured into ice water, and the mixture was made acidic with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, and recrystallized from methanol to obtain 2.9 g of 4-cinnamoylamino-3-methylbenzoic acid as a white powder.

Workup

  1. additionThereto was dropwise added, with ice-
  2. temperaturecooling
  3. customto give rise
  4. customto a reaction
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9c61d25f4f40453683cf50dca277638d
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Linked notes

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