p-Toluenesulfonic acid → HCID 70550907, compound

HRID 261035Notes

Reaction equation

HRID 261035 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:15]([C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=[O:21])(O)=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]=[C:15]1[C:18]2[C:19](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)[O:21]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8406Phthalaldehydic acidHCID 118009Ethyl 2-(4-aminophenyl)propanoate

Product 1

HCID 70550907HCID 70550907, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 17.7 g of ethyl α-(4-aminophenyl)-propionate, 15 g of 2-carboxy-benzaldehyde, 50 mg of p-toluenesulfonic acid and 400 ml of toluene is refluxed for two days on a water trap. After collection of the theoretical amount of water (1.9 ml), it is concentrated and the precipitate formed recrystallized from ethanol, to yield the ethyl α-[4-(3-oxo-isobenzofuran-1-ylamino)-phenyl]propionate, melting at 136°-139°.

Workup

  1. temperatureis refluxed for two days on a water trap
  2. customAfter collection of the theoretical amount of water (1.9 ml), it
  3. concentrationis concentrated
  4. customthe precipitate formed
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c261bcffac1940578e0169e9c08e24cc
Source dataset
uspto-grants-1979_08
Patent number
US04163788

Reaction notes

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