Formic Acid → HCID 20071081, compound

HRID 2291441Notes

Reaction equation

HRID 2291441 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([NH2:13])[CH:3]=1.C(O)=O>C(N(CC)CC)C.[Pd]>[NH2:13][C:4]1[CH:3]=[CH:2][CH:7]=[C:6]([NH:8][CH3:9])[C:5]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 20071066HCID 20071066, compound

Product 1

HCID 20071081HCID 20071081, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

59.5 mg of palladium at a concentration of 10% on charcoal are added to 0.014 mole (2.8 g) of 4-chloro-2-amino-6-methylaminonitrobenzene in 5.3 ml of triethylamine, and 1.16 ml of formic acid are then run in dropwise. A high exothermicity is noted. The reaction mixture is heated to 80° C. for 40 minutes. After dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration. The filtrate, evaporated under reduced pressure, enables a dry extract to be obtained. After dilution of the dry extract with water, the expected product precipitates. After being filtered off and washed with water, the precipitate is dried under vacuum in the presence of phosphorous pentoxide. After two recrystallizations from isopropanol in order to remove a gum, the product melts at 70° C.

Workup

  1. customAfter dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration
  2. customThe filtrate, evaporated under reduced pressure
  3. extractionextract
  4. customto be obtained
  5. extractionAfter dilution of the dry extract with water
  6. customthe expected product precipitates
  7. filtrationAfter being filtered off
  8. washwashed with water
  9. dry with materialthe precipitate is dried under vacuum in the presence of phosphorous pentoxide
  10. customAfter two recrystallizations from isopropanol in order
  11. customto remove a gum

Sources & evidence

ORD record
ord-d89d31a38b5243f298451116a366f3d0
Source dataset
uspto-grants-1989_01
Patent number
US04797129

Reaction notes

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