Sodium hydride → HCID 54332806, compound

HRID 1595177Notes

Reaction equation

HRID 1595177 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8](=[O:15])[NH:7]2)([O-:3])=[O:2].[H-].[Na+].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Br)[CH:22]=1>CN(C)C=O>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:10]2[C:11]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=3)[NH:7][C:8](=[O:15])[C:9]2=[O:14])[CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 40381426-NITROQUINOXALINE-2,3-DIONE

Product 1

HCID 54332806HCID 54332806, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an N2 stream and exclusion of moisture, 1.03 g (5 millimoles) of 6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline is combined with 50 ml of dimethylformamide at room temperature. To this mixture is added 330 mg (11 mmol) of sodium hydride (80% strength) in 3 portions. The mixture is then stirred for one hour at room temperature. To this mixture is added dropwise 1.26 g (5.5 mmol) of 3-bromomethyl-benzoic acid methyl ester in 5 ml of dimethylformamide, and the mixture is further stirred for 3½ hours. After concentration, the residue is distributed in acetic water/ethyl acetate. The organic phase is separated, dried, filtered and concentrated. The residue is chromatographed over silica gel with dichloromethan:ethanol=95:5, thus obtaining, besides 211 mg of 3-(6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl-methyl)benzoic acid methyl ester, which is not further purified, also 222 mg of 3-(7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-ylmethyl) benzoic acid methyl ester, mp: 265-267° C.

Workup

  1. stirringthe mixture is further stirred for 3½ hours
  2. concentrationAfter concentration
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed over silica gel with dichloromethan

Sources & evidence

ORD record
ord-bf57e4acbd0240649f055e9178fbfd4d
Source dataset
uspto-grants-2001_09
Patent number
US06288065B1

Reaction notes

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