p-Toluenesulfonic acid → HCID 21105459, compound

HRID 2426739Notes

Reaction equation

HRID 2426739 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-90b621e98de74068bb57f29579bf9c66
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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