p-Toluenesulfonic acid → HCID 10133309, compound

HRID 842198Notes

Reaction equation

HRID 842198 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:12]([O:14][C:15](=[O:29])[CH:16]([C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][C:18](=O)[CH3:19])[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:17]=[C:18]([CH3:19])[N:1]([C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[C:21]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:29])[CH3:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 10133309HCID 10133309, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-aminobenzoate (10 mmol, 1.4 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (10 mmol, 2.5 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The named product was purified over silica gel and crystallized upon standing, 1H-NMR (CDCl3, ppm): 1.15 t (3H), 2.08 s (3H), 3.88 s (3H), 4.05 q (2H), 6.56 s (1H), 7.15-7.33 bm (7H), 7.79-7.97 bm (2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe named product was purified over silica gel
  4. customcrystallized

Sources & evidence

ORD record
ord-ce43c89383094f7a8cf3e46415ac872b
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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