Ammonia → (4-Amino-3-nitrophenyl)-2-pyridinylmethanone

HRID 2399026Notes

Reaction equation

HRID 2399026 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=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:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20061086HCID 20061086, compound

Product 1

HCID 21432596(4-Amino-3-nitrophenyl)-2-pyridinylmethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 63 g. (0.24 mol) of 2-(3-nitro-4-chlorobenzoyl)pyridine in 3 liters of a saturated solution of ammonia in ethanol was autoclaved at 100° C. for 24 hrs. The mixture was concentrated in vacuo and the resulting residue dissolved in 1.5 liters of warm 5N hydrochloric acid. The solution was cooled to room temperature and neutralized with concentrated ammonium hydroxide. The resulting yellow product was collected, washed with water and dried to yield 2-(3-nitro-4-aminobenzoyl)pyridine, mp. 186° -187° C. (acetone-water).

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 hydrochloric acid
  4. customThe resulting yellow product was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a674d49c920044ebb9683997cb9c3e19
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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