Morpholine → (6-Nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester

HRID 618642Notes

Reaction equation

HRID 618642 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17](F)[CH:18]=2)[NH:13][C:12](=[O:24])[C:11]1=[O:25])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[CH2:1]([O:3][P:4]([CH2:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:18]=2)[NH:13][C:12](=[O:24])[C:11]1=[O:25])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 17800809(6-Nitro-7-fluoro-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester

Product 1

HCID 17800789(6-Nitro-7-morpholino-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl esterYield 181.8%

Procedure

140 mg of (6-nitro-7-fluoro-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester is heated with 129 mg of morpholine for 1.5 hours to 120° C. bath temperature. After concentration by evaporation in a vacuum, the residue is chromatographed on silica gel with toluene:glacial acetic acid:water=10:10:1. After concentration by evaporation of the corresponding fractions, 300 mg of (7-morpholino-6-nitro-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl)methanephosphonic acid diethyl ester is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation in a vacuum
  3. customthe residue is chromatographed on silica gel with toluene
  4. concentrationAfter concentration
  5. customby evaporation of the corresponding fractions

Sources & evidence

ORD record
ord-668f7d6b42e344dda9eb1a4cae6ea60a
Source dataset
uspto-grants-1999_09
Patent number
US05955461

Reaction notes

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