p-Toluenesulfonic acid → HCID 10133309, compound

HRID 413909Notes

Reaction equation

HRID 413909 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-2a39740c69ef47b9b6cfb932541ef09f
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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