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

HRID 1403293Notes

Reaction equation

HRID 1403293 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 56.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Iron (34.89 g, 623.04 mmol, 5.00 equiv) was added portionwise to a stirred solution of methyl 4-(2-methoxy-2-oxo-1-phenylethylamino)-3-nitrobenzoate (42.87 g, 124.62 mmol, 1.00 equiv) and aqueous NH4Cl (32.1 g, 600.00 mmol, 5.00 equiv, 80 mL) in methanol (300 mL). The resulting solution was heated under reflux for 5 h. Upon cooling, the solids were filtered out. The resulting filtrate was concentrated under vacuum, affording 19.81 g (56%) of methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate as a yellow solid. LC-MS (ES, m/z): 283 [M+H]+.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 5 h
  3. temperatureUpon cooling
  4. filtrationthe solids were filtered out
  5. concentrationThe resulting filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-6c9d455d18414de5ae4b496c291800ed
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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