p-Toluenesulfonic acid → [5-Methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetic acid

HRID 2051663Notes

Reaction equation

HRID 2051663 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]([C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:6]=1[CH3:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([C:16]([N:7]2[C:8]3[C:13](=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[C:6]2[CH3:27])=[O:26])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20379446HCID 20379446, compound

Product 1

HCID 12845005[5-Methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4.9 g (12.8 mmol) of methyl-1-(p-nitrobenzoyl)-5-methoxy-2-methyl-3-indolylacetate in 40 ml of acetic acid containing 400 mg of p-toluene-sulfonic acid is refluxed for 20 hours and then concentrated in vacuo. p The gummy residue is extracted with ethyl acetate.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionis extracted with ethyl acetate

Sources & evidence

ORD record
ord-ec2613ae136d49028be3f35a3a910d7c
Source dataset
uspto-grants-1980_01
Patent number
US04181740

Reaction notes

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