Ethanol → 8-bromo-3,4-dihydro-1H-quinoxalin-2-one

HRID 216726Notes

Reaction equation

HRID 216726 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:8]=1[N+:14]([O-])=O)C.CCO>C1COCC1.[Ni]>[Br:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]2[C:8]=1[NH:14][C:4](=[O:3])[CH2:5][NH:6]2

Participants

5

Reactant 2

HCID 702EthanolHCID 59392671(3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

Product 1

HCID 593926768-bromo-3,4-dihydro-1H-quinoxalin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10.33 g (ca. 25.9 mmol) (3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester is hydrogenated in the presence of 2.84 g Ra—Ni (B113W EtOH, Degussa) in 340 ml of THF:EtOH=1:1 for 20 h. The reaction mixture is filtered on hyflo and the filtrate is concentrated in vacuo. A mixture of the title compound with uncyclized (2-Amino-3-bromo-phenylamino)-acetic acid ethyl ester is obtained and used as obtained in the next synthetic step.

Workup

  1. filtrationThe reaction mixture is filtered on hyflo
  2. concentrationthe filtrate is concentrated in vacuo
  3. additionA mixture of the title compound with uncyclized (2-Amino-3-bromo-phenylamino)-acetic acid ethyl ester
  4. customis obtained
  5. customas obtained in the next synthetic step

Sources & evidence

ORD record
ord-2563426f1ac34776be927d7126bc94dd
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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