Ammonia → 4-Nitro-2,3-dihydro-1H-isoindol-1-one

HRID 1862084Notes

Reaction equation

HRID 1862084 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13]Br.[NH3:16]>CO>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[CH2:13][NH:16][C:3]2=[O:2])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Product 1

HCID 219613874-Nitro-2,3-dihydro-1H-isoindol-1-oneYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-2-bromomethyl-3-nitro-benzoate (6.9 gm, 0.025 mol.) in methanol, was added slowly a methanolic solution of ammonia (50 ml), and the reaction mixture was stirred at room temperature for 2 hr. The pale yellow colored solid separated out was filtered, dried under vacuum to give 4-nitro-2,3-dihydro-1H-isoindol-1-one (compound 3, 3.570 gm, 81%).

Workup

  1. customThe pale yellow colored solid separated out
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-58ffae79374149f59d2a112fdb4765c1
Source dataset
uspto-grants-2003_03
Patent number
US06534651B2

Reaction notes

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