Diisopropylethylamine → Diethyl N-(2,3-dimethoxy-7-nitroquinoxalin-5-ylmethyl)-2-aminophenylphosphonate

HRID 1953784Notes

Reaction equation

HRID 1953784 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:26]=[CH:25][CH:24]=[CH:23][C:22]=1[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].C(N(C(C)C)CC)(C)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:26]=[CH:25][CH:24]=[CH:23][C:22]=2[P:27](=[O:34])([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33])[N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12482984Diethyl (2-aminophenyl)phosphonateHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 23297993Diethyl N-(2,3-dimethoxy-7-nitroquinoxalin-5-ylmethyl)-2-aminophenylphosphonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

190 mg (0.579 mmol) of 5-bromomethyl-7-nitro-2,3-dimethoxyquinoxaline, 159 mg (1.2 eq.) of diethyl 2-aminophenylphosphonate and 0.2 ml (2 eq.) of diisopropylethylamine are stirred at reflux for 20 hours in 8 ml of acetonitrile. The reaction mixture is evaporated and the residue is extracted with water and ethyl acetate. The combined organic phases are dried using brine and magnesium sulfate and evaporated. The title compound is obtained as a yellow solid.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionthe residue is extracted with water and ethyl acetate
  3. customThe combined organic phases are dried
  4. customevaporated

Sources & evidence

ORD record
ord-5c1987d5ec6240529002594ae1d4839e
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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