Ethyl bromoacetate → HCID 54140021, compound

HRID 1870219Notes

Reaction equation

HRID 1870219 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:14])[C:8](=[O:13])[N:9]2[OH:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[Cl-].[NH4+]>CN(C=O)C>[O:13]=[C:8]1[C:7](=[O:14])[NH:6][C:5]2[C:10](=[CH:11][C:2]([F:1])=[C:3]([N+:15]([O-:17])=[O:16])[CH:4]=2)[N:9]1[O:12][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10538061HCID 10538061, compound

Product 1

HCID 54140021HCID 54140021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of DMF, 500 mg of 7-fluoro-1-hydroxy-6-nitro-2,3(1H,4H)-quinoxalinedione was dissolved. To the aresulting solution, 83 mg of sodium hydride was added, followed by stirring for 10 minutes. To the reaction -z mixture, 218 ml of ethyl bromoacetate was added, followed by reaction for 2 days. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with chloroform three times. The organic layer was concentrated, followed by recrystallization from 2-propanol to give 481 mg of ethyl 2-[(2,3-dioxo-7-fluoro-6-nitro-1,2,3,4-tetrahydroquinoxalinyl)oxy]acetate.

Workup

  1. customfollowed by reaction for 2 days
  2. extractionfollowed by extraction with chloroform three times
  3. concentrationThe organic layer was concentrated
  4. customfollowed by recrystallization from 2-propanol

Sources & evidence

ORD record
ord-7c428754ab7043419521839f944b96a0
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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