p-Toluenesulfonic acid → HCID 21105459, compound

HRID 1354792Notes

Reaction equation

HRID 1354792 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C([O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH2:19][C:18]1=O)=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:14]=[C:15]1[CH:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[N:2][N:1]1[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 120894-Hydrazinobenzoic acidHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 21105459HCID 21105459, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-hydrazinobenzoic acid (0.3 g), ethyl-2-oxocyclopentanecarboxylate (0.31 g) and p-toluenesulfonic acid (340 mg) in ethanol (12 ml) was boiled under reflux for 12 hours. The concentrated reaction solution was purified by preparative HPLC. The isolated reaction product (as ethyl ester) was hydrolyzed by method P-a. This resulted in the product with the molecular weight of 244.25 (C13H12N2O3); MS (ESI): 245 (M+H+).

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe concentrated reaction solution
  3. customwas purified by preparative HPLC
  4. customThe isolated reaction product (as ethyl ester)
  5. customThis resulted in the product with the molecular weight of 244.25 (C13H12N2O3)

Sources & evidence

ORD record
ord-dcfaa5677afc4d35b352659587f6795e
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…