N-bromobutanimide → 5-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

HRID 1422215Notes

Reaction equation

HRID 1422215 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:5](=[CH:6][C:7]([N+:16]([O-:18])=[O:17])=[CH:8][C:9]=2[CH3:15])[N:4]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:15][C:9]1[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=[C:5]2[C:10]=1[N:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[N:4]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 187064222,3-Dimethoxy-5-methyl-7-nitro-quinoxaline

Product 1

HCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 0.249 g (1.0 mmol) of 2,3-dimethoxy-5-methyl-7-nitro-quinoxaline, 0.178 g (1 mmol) of N-bromosuccinimide and 0.016 g (0.1 mmol) of azo-isobutyronitrile in 3 ml of CCl4 is heated at reflux for 20 hours. The reaction mixture is washed with water and brine and concentrated using a rotary evaporator. Crystallization from ethyl acetate yields the title compound. TLC: hexane/ethyl acetate 6/1: Rf=0.63, 1H-NMR (CDCl3): δ 8.64 (d, J=3, 1H), 8.41 (d, J=3, 1H), 5.02(s, 2H), 4.27(s, 3H), 4.20 (s, 3H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hours
  3. washThe reaction mixture is washed with water and brine
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2fb8a1abe02e4516be867a3a3b136f74
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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