Methyl 4-cyano-2-methylbenzoate → 1-Oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

HRID 1846218Notes

Reaction equation

HRID 1846218 reaction equation
C(C1C=CC(C([O:9][CH3:10])=O)=C(C)C=1)#N.Br[C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17](C)[CH:16]=1.[C:26]([Cu])#[N:27]>CN(C=O)C.CCOC(C)=O>[O:9]=[C:10]1[C:15]2[C:16](=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=2)[CH2:26][NH:27]1

Participants

6

Reactant 3

HCID 18766060Methyl 4-cyano-2-methylbenzoateHCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 128502661-Oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
175 °C

Procedure

methyl 4-cyano-2-methylbenzoate. To a stirred solution of methyl 4-bromo-2-methylbenzoate (2 g, 8.7 mmol) in DMF (20 mL), was added CuCN (1.9 g, 12.2 mmol). The reaction was then stirred at 175° C. for 6 h. The progress of the reaction was monitored by TLC (10% EtOAc in hexanes). The reaction was diluted with EtOAc (10 mL) and filtered through Celite® brand filtering agent. The filtrate was concentrated in vacuo and the material was purified by column chromatography (SiO2, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 177.1 (MH+).

Workup

  1. filtrationfiltered through Celite® brand
  2. filtrationfiltering agent
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe material was purified by column chromatography (SiO2, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-622c5cf8e56c4976af53bc9bc31247f3
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

Loading…