Hydrochloric Acid → 4'-Methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid

HRID 418396Notes

Reaction equation

HRID 418396 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH:8]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]2=[O:20])[CH:10]=1)=[O:4].O.[OH-].[Na+].Cl>CO.C1COCC1>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([C:7]2[CH:8]=[C:9]([N:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][C:12]3=[O:20])[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 596277454'-Methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 596277614'-Methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude 4′-methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid methyl ester from step 2 was in a mixture of methanol (3 mL), water (1 mL) and THF (1 mL), and 2M aqueous NaOH (0.4 mL) was added. The mixture was stirred for 2.5 hours, then neutralized by addition of 1N aqueous HCl. The mixture was concentrated under reduced pressure and co-evaporated with toluene three times to afford crude 4′-methyl-5-(2-oxo-2,3-dihydro-indol-1-yl)-biphenyl-3-carboxylic acid, which was used directly in the next step.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated under reduced pressure and co-evaporated with toluene three times

Sources & evidence

ORD record
ord-68ae30697da74246bf0289577a94fe71
Source dataset
uspto-grants-2012_01
Patent number
US08093275B2

Reaction notes

Loading…