N-Benzylglycine ethyl ester → HCID 22667730, compound

HRID 844134Notes

Reaction equation

HRID 844134 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C([O:14][C:15](=[O:25])[CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:17]([CH2:16][C:15]([OH:25])=[O:14])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 80908N-Benzylglycine ethyl esterHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 22667730HCID 22667730, compoundYield 55%

Procedure

In a manner as described above, 4-bromo-2-fluoro-1-nitro-benzene (11 g, 50 mmol), and N-benzyl-glycine ethyl ester (10 g, 50 mmol) were reacted to give crude [(5-bromo-nitro-phenyl)-benzyl-amino]-acetic acid (10 g, 55%). This product was reacted with iron powder to obtain crude 4-benzyl-6-bromo-3,4-dihydroquinoxalin-2(1H)-one (5 g, 58%). A sample was recrystallized from ethyl acetate/hexane: m.p. 174-176° C. 1H-NMR (DMSO-d6) δ3.75 (s, 2H), 4.43 (s, 2H), 6.71 (d, J=1.9 Hz, 1H), 6.81 (m, 2H), 7.32 (m, 5H), 10.57 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6785d5a34b9f483f96181e75eb232b87
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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