Ammonium Chloride → Methyl 2-(3,4-diaminophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

HRID 1403519Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25][CH3:26])=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:27]([O-])=O.[NH4+].[Cl-]>CO.O.[Fe]>[NH2:27][C:3]1[CH:4]=[C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]([O:25][CH3:26])=[O:24])[CH:14]=3)[N:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-(4-amino-3-nitrophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (900 mg, 2.28 mmol) in methanol (40 mL) was added iron (1.28 g, 22.8 mmol) and NH4Cl (1.81 g, 34.2 mmol). After stirring for 6 h at 60° C., the solids were filtered out. The filtrate was concentrated under vacuum to give a residue which was dissolved in water (200 mL), extracted with dichloromethane (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford methyl 2-(3,4-diaminophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as yellow solid (635 mg, crude).

Workup

filtrationthe solids were filtered out
concentrationThe filtrate was concentrated under vacuum
customto give a residue which
extractionextracted with dichloromethane (3×50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-59d523a3b4394aab9d14dc1bd759967e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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