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

HRID 2212699Notes

Reaction equation

HRID 2212699 reaction equation
[NH3:1].C[O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:14]Br>CO>[N+:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]2[C:6]=1[CH2:14][NH:1][C:4]2=[O:3])([O-:13])=[O:12]

Participants

4

Reactant 2

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

Product 1

HCID 219613874-Nitro-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NH3 (2.0 M in MeOH, 50 ml) was slowly added to the solution of 2-bromomethyl-3-nitro-benzoic acid methyl ester (4.46 g, contaminated with a small amount of assumed starting material, 16.3 mmol) in 30 ml of MeOH at RT. The resulting mixture was stirred at RT overnight, to provide the title compound as a white solid. MS (ES+): 179.2 (M+H)+. Calc'd for C8H6N2O3—178.14.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-dd3110399a334ff78435c7655358abcb
Source dataset
uspto-grants-2006_09
Patent number
US07102009B2

Reaction notes

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