3-Aminobenzoic Acid → N-[2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl]-3-amino-benzoic acid

HRID 1422238Notes

Reaction equation

HRID 1422238 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2.[NH2:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([OH:26])=[O:25].C(N(CC)CC)C>C(#N)C>[CH3:17][O:16][C:7]1[C:6]([O:18][CH3:19])=[N:5][C:4]2[C:9](=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[CH2:2][NH:20][C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=[O:25])[N:8]=1

Participants

5

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 8471TriethylamineHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 18706361N-[2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl]-3-amino-benzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

350 mg (1.06 mmol) of 5-bromomethyl-2,3-dimethoxy-7-nitro-quinoxaline, 153 mg (1.05 equiv.) of 3-aminobenzoic acid and 0.165 ml (1.1 equiv.) of triethylamine are combined in 10 ml of acetonitrile, and heated at boiling at reflux for 24 hours. The reacton mixture is concentrated by evaporation, extracted with ethyl acetate and 1 N HCl and washed once with brine. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. concentrationThe reacton mixture is concentrated by evaporation
  4. extractionextracted with ethyl acetate and 1 N HCl
  5. washwashed once with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2293684384ae44e8b2c3620ad608b5a4
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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