Ammonia → 3-(3-Nitro-4-aminobenzoyl)pyridine

HRID 2399035Notes

Reaction equation

HRID 2399035 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1Cl)[C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8])([O-:3])=[O:2].[NH3:19]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:19])[C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 214326003-(3-Nitro-4-chlorobenzoyl)pyridine

Product 1

HCID 214325873-(3-Nitro-4-aminobenzoyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 63 g. (0.24 mol) of 3-(3-nitro-4-chlorobenzoyl)pyridine in 3 liters of a saturated solution of ammonia in ethanol was autoclaved at 100° C. for 24 hours. The mixture was concentrated in vacuo and the resulting residue dissolved in 1.5 liters of warm 5N HCl. The solution was cooled to room temperature and neutralized with concentrated ammonium hydroxide. The resulting product was collected as yellow-orange prisms, mp. 229° -230° C. (dimethylformamide-2-propanol).

Workup

  1. additionA suspension of 63 g
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe resulting residue dissolved in 1.5 liters of warm 5N HCl
  4. customThe resulting product was collected as yellow-orange prisms, mp. 229° -230° C. (dimethylformamide-2-propanol)

Sources & evidence

ORD record
ord-cec53df07eca460888cad9af9ad2a29e
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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