Ammonia → HCID 15219320, compound

HRID 1109839Notes

Reaction equation

HRID 1109839 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1Br)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19](Br)=[C:18]([N+:23]([O-])=O)[CH:17]=2)[CH:10]=1)=[O:8])([O-])=O.[H][H].N>[Pd].C(O)(C)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:23])[CH:17]=2)[CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19708203HCID 19708203, compoundHCID 178418361HCID 178418361, compound4×

Product 1

HCID 15219320HCID 15219320, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a sealed glass reaction vessel equipped with a thermometer, stirrer and reflux condenser, 10.7 g (0.02 mole) of 1,3-bis(3-nitro-4-bromobenzoyl)benzene, 0.43 g of a 5% palladium/activated carbon catalyst (a product of M. E. Chemcat Co.) and 50 ml of isopropyl alcohol were charged. Hydrogen was introduced with stirring at 30°~35° C. Absorbed hydrogen was 2.20 l (0.098 mole) over 9 hours. Successively, 3.6 g (0.06 mole) of a 28% aqueous ammonia solution was added and introduction of hydrogen was continued at 30°~35° C. for 6 hours and additionally at 60° C. for 4 hours with stirring. Further absorbed hydrogen was 0.401 g (0.018 mole). The catalyst was removed by filtration at the same temperature, 4.5 g of a 36% aqueous hydrochloric acid solution was added to the filtrate, and the mixture was allowed to cool. The precipitated crystal of 1,3-bis(3-aminobenzoyl)benzene hydrochloride were filtered, dissolved in 200 ml of water, and neutralized with a 28% aqueous ammonia solution. The precipitated crystals were filtered, washed and dried to obtain 1.9 g of 1,3-bis(3-aminobenzoyl)benzene. The yield was 30%.

Workup

  1. customTo a sealed glass reaction vessel
  2. customequipped with a thermometer, stirrer
  3. temperaturereflux condenser
  4. customover 9 hours
  5. stirringwith stirring
  6. customThe catalyst was removed by filtration at the same temperature, 4.5 g of a 36% aqueous hydrochloric acid solution
  7. additionwas added to the filtrate
  8. temperatureto cool
  9. filtrationThe precipitated crystal of 1,3-bis(3-aminobenzoyl)benzene hydrochloride were filtered
  10. dissolutiondissolved in 200 ml of water
  11. filtrationThe precipitated crystals were filtered
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-13282579971b443f8ae4ebc5ecce84ad
Source dataset
uspto-grants-1994_06
Patent number
US05322962

Reaction notes

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