Ammonia → 7-bromo-5-nitroisoquinolin-1(2H)-one

HRID 577597Notes

Reaction equation

HRID 577597 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][O:8][C:9]2=O)=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[NH3:16]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:16][C:9]2=[O:8])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 867238247-bromo-5-nitro-1H-isochromen-1-one

Product 1

HCID 825721717-bromo-5-nitroisoquinolin-1(2H)-oneYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A sealed tube containing 7-bromo-5-nitro-1H-isochromen-1-one (293a, 9.20 g, 34.1 mmol) and 7 N ammonia solution in methanol (100 mL) was stirred at 60° C. overnight. After chilling in an ice bath, the resulting precipitate was collected by filtration, washed with cold methanol, and air-dried to give 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 7.6 g, 83% yield). as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 11.82 (br. s., 1H), 8.56-8.64 (m, 2H), 7.48 (d, J=7.58 Hz, 1H), 6.89 (d, J=7.58 Hz, 1H). MS: 267/269 [M−1].

Workup

  1. temperatureAfter chilling in an ice bath
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with cold methanol
  4. customair-dried

Sources & evidence

ORD record
ord-8697ef7c67ca4b70960db1d124b721e8
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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