1-Carbethoxycarbonylmethyl-2-amino-3-carbamoyl-quinoxalinium bromide → Ethyl 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylate

HRID 126774Notes

Reaction equation

HRID 126774 reaction equation
[Br-].[C:2]([C:7]([CH2:9][N+:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([C:20](=[O:22])[NH2:21])[C:11]=1[NH2:23])=O)([O:4][CH2:5][CH3:6])=[O:3]>C(O)C>[C:20]([C:12]1[C:11]2[N:10]([CH:9]=[C:7]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:23]=2)[C:19]2[C:14]([N:13]=1)=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:22])[NH2:21]

Participants

3

Reactant 1

HCID 202879831-Carbethoxycarbonylmethyl-2-amino-3-carbamoyl-quinoxalinium bromide

Product 1

HCID 14067521Ethyl 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylateYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1 g of the product of Step A in 100 ml of ethanol was refluxed with stirring for 90 minutes and the resulting yellow solution was concentrated and cooled. The mixture was filtered to obtain 0.55 g of ethyl 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylate as a pale yellow crystalline solid. Recrystallization from ethanol yielded soft white needles melting at 280°-284° C.

Workup

  1. temperaturewas refluxed
  2. concentrationthe resulting yellow solution was concentrated
  3. temperaturecooled
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-f314d70b542d41eeba794cd016ca4891
Source dataset
uspto-grants-1981_03
Patent number
US04254123

Reaction notes

Loading…