Citric Acid → HCID 10423236, compound

HRID 2089273Notes

Reaction equation

HRID 2089273 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[N+:17]([O-])=[O:18])=[CH:4][CH:3]=1.C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO.CN(C=O)C.O>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([C:5]3[CH:20]=[CH:21][C:2]([NH2:1])=[CH:3][CH:4]=3)[N:17]([OH:18])[C:9]=2[CH:10]=1)([O-:16])=[O:15]

Participants

7

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 44254850HCID 44254850, compound

Product 1

HCID 10423236HCID 10423236, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-aminobenzyl)-2,4-dinitroaniline (7) (21.6 g, 74.9 mmol) in anhydrous EtOH (300 mL) and anhydrous DMF (75 mL) was slowly added sodium methoxide (30% w/w) (69.1 g, 375 mmol) at room temperature under argon atmosphere, followed by heating to 60° C. for 2 hours. After cooling to ambient termperature, the solution was diluted with water (700 mL) and then acidified with saturated citric acid. The resulting precipitate was collected on a sintered funnel while rinsing with water. The crude product was recrystallized in hot EtOH to afford 18.1 g as a brown solid in 90% yield.

Workup

  1. customat room temperature
  2. temperatureAfter cooling to ambient termperature
  3. customThe resulting precipitate was collected on a sintered funnel
  4. washwhile rinsing with water
  5. customThe crude product was recrystallized in hot EtOH
  6. customto afford 18.1 g as a brown solid in 90% yield

Sources & evidence

ORD record
ord-8316dbab2b1042bca046377b3a524b4a
Source dataset
uspto-grants-2013_05
Patent number
US08436031B2

Reaction notes

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