Nitronium tetrafluoroborate → 9-Bromo-5-(1-methoxycarbonylethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52546Notes

Reaction equation

HRID 52546 reaction equation
[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([C:14](OCC)=[O:15])=[O:13])[CH:7]([CH:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])[CH2:6][CH2:5]2.F[B-](F)(F)F.O=[N+:31]=O.[N+]([O-])([O-])=O.[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:5][CH2:6][CH:7]([CH:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])[N:8]3[C:12](=[O:13])[C:14](=[O:15])[NH:31][C:10]([CH:11]=1)=[C:9]23

Participants

6

Reactant 3

HCID 11073463Nitronium tetrafluoroborateHCID 67722033HCID 67722033, compoundHCID 86750628Ammonium nitrate trifluoroacetic anhydride

Product 1

HCID 541191439-Bromo-5-(1-methoxycarbonylethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the route outlined in Example 22-6 to 7 starting with 6-bromo-N-ethoxalyl-2-(1-methoxycarbonylethyl)tetrahydroquinoline (more polar). In nitration step of Example 22-6, conditions of nitronium tetrafluoroborate in dichloromethane at room temperature were employed instead of those of refluxing ammonium nitrate-trifluoroacetic anhydride in chloroform: mp 256°~257° C.; 1H NMR (270 MHz, DMSO-d6) δ12.12 (s, 1H), 7.19 (s, 1H), 7.16 (s, 1H), 5.11 (bd, 1H, J=9 Hz), 3.58 (s, 3H), 2.89 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.72~2.87 (m, 2H), 2.03 (dm, 1H, J=13.5 Hz), 1.76~1.94 (m, 1H), 0.97 (d, 3H, J=7 Hz).

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-79b618c3f26f49f888d92531dcb68b32
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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