Ammonia → 7-Nitro-2,3-dihydro-1H-isoindol-1-one

HRID 2112071Notes

Reaction equation

HRID 2112071 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:4]=1[C:5](OC)=[O:6].[NH3:16]>CN(C)C=O.C(OCC)(=O)C>[N+:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:3]2[C:4]=1[C:5](=[O:6])[NH:16][CH2:2]2)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 162279487-Nitro-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 g (5.473 mmol) methyl 2-bromomethyl-6-nitro-benzoate are dissolved in 20 ml N,N-dimethylformamide and combined with 15 ml of methanolic ammonia (7 mmol/ml). After 20 h at 25° C. the mixture is diluted with 100 ml of ethyl acetate and extracted 3 times with saturated sodium hydrogen carbonate solution. The organic phase is dried with magnesium sulphate and the solvent is eliminated in vacuo.

Workup

  1. extractionextracted 3 times with saturated sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried with magnesium sulphate

Sources & evidence

ORD record
ord-7e6e6f8518774a88b8ab98d7ef9c973d
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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