Sodium Nitrite → HCID 178497314, compound

HRID 1403520Notes

Reaction equation

HRID 1403520 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]([N:19]([CH:21]([CH3:23])[CH3:22])[CH3:20])=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:24]([O:26][CH3:27])=[O:25])[CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[N:28]([O-])=O.[Na+]>Cl.O>[NH:8]1[C:7]2[CH:6]=[CH:5][C:4]([C:9]3[C:18]([N:19]([CH:21]([CH3:23])[CH3:22])[CH3:20])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:24]([O:26][CH3:27])=[O:25])[CH:15]=4)[N:10]=3)=[CH:3][C:2]=2[N:1]=[N:28]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 70664805Methyl 2-(3,4-diaminophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 178497314HCID 178497314, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(3,4-diaminophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (635 mg, crude) in HCl (1N, 150 mL) was added sodium nitrite (132 mg, 1.91 mmol) in water (1 mL) at 0° C. After stirring for 15 min at 0° C., the reaction mixture was extracted with dichloromethane (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (3% methanol in dichloromethane) to afford methyl 2-(1H-benzo[d][1,2,3]triazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid (140 mg).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (3×50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified via silica gel chromatography (3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fef979e5182c4756a0f6102ac715b14d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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