Nitronium tetrafluoroborate → HCID 23206548, compound

HRID 1289433Notes

Reaction equation

HRID 1289433 reaction equation
[CH2:1]([O:3][P:4]([CH:9]1[N:14]2[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]3[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:12]([C:13]=32)[CH2:11][CH2:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].F[B-](F)(F)F.[O:33]=[N+:34]=[O:35]>ClCCl>[CH2:6]([O:5][P:4]([CH:9]1[N:14]2[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]3[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:21]([N+:34]([O-:35])=[O:33])=[C:12]([C:13]=32)[CH2:11][CH2:10]1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 15225059HCID 15225059, compound

Product 1

HCID 23206548HCID 23206548, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

812 mg of 9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid diethyl ester is dissolved in 15 ml of dichloromethane and mixed with 531 mg of nitronium tetrafluoroborate at room temperature. It is stirred for 15 hours and concentrated by evaporation. The residue is taken up in ethyl acetate and washed with 5% sodium bicarbonate solution. After column chromatography, 470 mg of 8-nitro-9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid diethyl ester of melting point 254° C. is obtained.

Workup

  1. concentrationconcentrated by evaporation
  2. washwashed with 5% sodium bicarbonate solution

Sources & evidence

ORD record
ord-71a657f347184f9481b06df6d6aedf55
Source dataset
uspto-grants-1998_05
Patent number
US05750526

Reaction notes

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