Ammonium Chloride → Methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

HRID 2205097Notes

Reaction equation

HRID 2205097 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[N+:22]([O-])=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH4+].[Cl-]>CO.[Fe]>[O:2]=[C:3]1[NH:22][C:13]2[C:12](=[CH:21][CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=2)[NH:11][CH:4]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67980137Methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate

Product 1

HCID 67042084Methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylateYield 277.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate (350 mg, 1.02 mmol, 1.00 equiv) in MeOH (10 mL) was added Fe (280 mg, 5.00 mmol, 5.00 equiv) and saturated NH4Cl (3 mL), and the resulting solution was allowed to react, with stifling, for 2 hrs while the temperature was maintained at reflux in an oil bath. The solids were collected by filtration and discarded. The resulting solution was concentrated under vacuum giving 0.8 g (crude) of methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customto react
  2. temperaturewas maintained
  3. temperatureat reflux in an oil bath
  4. filtrationThe solids were collected by filtration
  5. concentrationThe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-0092969d3a7c4e90a1bde0300fc59703
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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