p-Toluenesulfonic acid → HCID 19599436, compound

HRID 1458629Notes

Reaction equation

HRID 1458629 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.CO[CH:17](OC)[CH2:18][CH:19](OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[N:1]1[C:2]2=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66019TetramethoxypropaneHCID 15154323Methyl 2-amino-1H-indole-3-carboxylate

Product 1

HCID 19599436HCID 19599436, compound

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 I, 1992, 275) (0.5 g, 0.0026 mole) in xylene (10 ml) was treated with 1,1,3,3-tetramethoxypropane (0.43 g, 0.0026 mole) and a few crystals of 4-toluenesulphonic acid and heated under reflux for 2.5 h. The mixture was concentrated in vacuo and the residue dissolved in chloroform (25 ml), washed with water (2×10 ml), dried (MgSO4) and concentrated in vacuo to leave a dark orange solid. This was purified by chromatography on silica gel eluting with ethyl acetate to afford the title compound (D19) as an orange solid (0.23 g, 35%).

Workup

  1. temperatureunder reflux for 2.5 h
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in chloroform (25 ml)
  4. washwashed with water (2×10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto leave a dark orange solid
  8. customThis was purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-0977fd2c156345e088f5813a312f6464
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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