Hydrochloric Acid → HCID 66772119, compound

HRID 1645263Notes

Reaction equation

HRID 1645263 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23]C)=[O:22])[O:5][C:6]=1[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17].Cl>CCO.[OH-].[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([OH:23])=[O:22])[O:5][C:6]=1[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66772508HCID 66772508, compound

Product 1

HCID 66772119HCID 66772119, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 3-(4-methyl-5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoate (125 mg, 0.35 mmol) in EtOH (5.0 mL) and NaOH (3N, 3.0 mL) was heated at 80° C. for 30 min. The reaction mixture was cooled to rt and pH was adjusted (pH=4) with HCl (6N). The resulting precipitate was collected by filtration to give the desired 3-(4-methyl-5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoic acid (95 mg). LCMS (ES): m/z 346 [M+1]+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-ab4f8bc37c054de3bf68d331aaa1ecc3
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

Loading…