2-Carboxy-5-nitrobenzeneacetamide → 6-nitroisoquinoline-1,3(2H,4H)-dione

HRID 2236557Notes

Reaction equation

HRID 2236557 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13][C:14]([NH2:16])=[O:15])(O)=[O:2]>ClC1C=CC=CC=1Cl>[N+:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:1](=[O:2])[NH:16][C:14](=[O:15])[CH2:13]2)([O-:12])=[O:11]

Participants

3

Reactant 1

HCID 593000362-Carboxy-5-nitrobenzeneacetamide

Product 1

HCID 592999676-nitroisoquinoline-1,3(2H,4H)-dioneYield 72.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A stirred suspension of 11.1 g (49.3 mmol) of 2-carboxy-5-nitrobenzeneacetamide in 99 ml of 1,2-dichlorobenzene is refluxed for 3 h. The residue obtained after evaporation of the solvent under vacuum is washed with ether and dried to give 7.34 g (72%) of a tan solid, mp 255-260° (dec); 1H NMR (DMSO-d6) δ 11.6 (s, 1H), 8.2-8.3 (m, 3H), 4.17 (s, 2H); MS (ES−) m/z 205.2 (M−H)−

Workup

  1. temperatureis refluxed for 3 h
  2. customThe residue obtained
  3. customafter evaporation of the solvent under vacuum
  4. washis washed with ether
  5. customdried

Sources & evidence

ORD record
ord-883b462a15c642618599de7d8422cbdc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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