HCID 21432597, compound → HCID 21432585, compound

HRID 2399037Notes

Reaction equation

HRID 2399037 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:7]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:8])([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:7]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 2

HCID 21432597HCID 21432597, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21432585HCID 21432585, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 20 g. (0.082 mol) of 4-(3-nitro-4-aminobenzoyl)pyridine in 1 liter of tetrahydrofuran containing 5 g. of 5% palladium on carbon was reduced with hydrogen under a pressure of 3 atmospheres. The resulting mixture was filtered and concentrated in vacuo to reddish oil which was dissolved in a minimum amount of methylene chloride and diluted with petroleum ether to yield 4-(3,4-diaminobenzoyl)pyridine as an unstable orange solid, mp. 210° -214° C. (water-Norite).

Workup

  1. additionA suspension of 20 g
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionwas dissolved in a minimum amount of methylene chloride
  5. additiondiluted with petroleum ether

Sources & evidence

ORD record
ord-c16edc4706114d9e8fa216940c33eeec
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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