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Formic Acid → 2-Nitrobenzene-1,3-diamine

HRID 2291436
Notes
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Reaction equation

HRID 2291436 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:3]=1.C(O)=O>C(N(CC)CC)C.[Pd]>[NH2:8][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([NH2:12])[C:5]=1[N+:9]([O-:11])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 284Formic AcidHCID 20071078HCID 20071078, compound

Product 1

HCID 141474902-Nitrobenzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

68 mg of palladium at a concentration of 10% on charcoal are added to 0.016 mole (3 g) of 4-chloro-2,6-diaminonitro-benzene in 6 ml of triethylamine, and 1.32 ml of formic acid are then added dropwise. A high exothermicity is noted. The reaction medium is heated to 90° C. for 1 hour 30. After dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration. The filtrate, evaporated to dryness under reduced pressure, enables a dry extract to be obtained. After dilution of the dry extract with water, the expected product precipitates. After filtration and washing with water, followed by drying under vacuum in the presence of phosphorus pentoxide, it is recrystallized from toluene. It melts at 142° C. (literature 141° C., 145° C.).

Workup

  1. additionare then added dropwise
  2. customAfter dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration
  3. customThe filtrate, evaporated to dryness under reduced pressure
  4. extractionextract
  5. customto be obtained
  6. extractionAfter dilution of the dry extract with water
  7. customthe expected product precipitates
  8. filtrationAfter filtration
  9. washwashing with water
  10. dry with materialby drying under vacuum in the presence of phosphorus pentoxide, it
  11. customis recrystallized from toluene
  12. customIt melts at 142° C. (literature 141° C., 145° C.)

Sources & evidence

ORD record
ord-39cb9675c051491487a1a909b8fdb6da
Source dataset
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04797129

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes