HCID 54010783, compound → 2-[1-(7-chloroquinolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid

HRID 597047Notes

Reaction equation

HRID 597047 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[CH:14]([CH2:23][C:24]([OH:26])=[O:25])[CH:13]3[CH3:27])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([OH:26])=[O:25])=[C:13]3[CH3:27])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54010783HCID 54010783, compound2×

Product 1

HCID 102373692-[1-(7-chloroquinolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindolin-3-ylacetic acid (1g.) and 2,3,5,6-tetrachloro-1,4-benzoquinone (1g.) in dry xylene (50ml.) was refluxed for 2 hours. The solvent was removed in vacuo and the residue adsorbed on a column of chromatographic silica gel (50g.). The column was eluted with chloroform containing increasing amounts of methanol (starting with pure chloroform, and then using increments of 1% v/v of methanol in chloroform; product mainly eluted with 5% methanol in chloroform) to give 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid, m.p. 248°-250° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed in vacuo
  3. washThe column was eluted with chloroform containing
  4. temperatureincreasing amounts of methanol (
  5. washproduct mainly eluted with 5% methanol in chloroform)

Sources & evidence

ORD record
ord-a6c3262e8b3a46b7b88e2c71d90c715e
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

Loading…