p-Toluenesulfonic acid → HCID 19599434, compound

HRID 1458627Notes

Reaction equation

HRID 1458627 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:15][C:16](=O)[CH2:17][C:18](=O)[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:15][C:16]1[CH:17]=[C:18]([CH3:19])[N:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31261AcetylacetoneHCID 15154323Methyl 2-amino-1H-indole-3-carboxylate

Product 1

HCID 19599434HCID 19599434, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution of methyl 2-aminoindole-3-carboxylate (I. Forbes et al, J. Chem. Soc. Perkin 1, 1992, 275) (0.25 g, 0.0013 mole) in xylene (5 ml) was treated with 2,4-pentanedione (0.13 g, 0.0013 mole) and a few crystals of 4-toluenesulphonic acid and heated under reflux for 2 h. The mixture was concentrated in vacuo and the residue dissolved in chloroform (20 ml), washed with water (2×20 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a brown solid (0.25 g, 75%).

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in chloroform (20 ml)
  4. washwashed with water (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92417b4ef8a642039ebd5c6ee126b8b0
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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