Hydrochloric Acid → 3-nitro-N-phenylpyridin-4-amine

HRID 324278Notes

Reaction equation

HRID 324278 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O.COCCO>[C:12]1([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 6120053-nitro-N-phenylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 22504935Water 2-methoxyethanolSolvent

Procedure

A solution of 4-chloro-3-nitropyridine (II: R′=4-aza, halogen=Cl) (3.22 g, 0.020 mol), aniline (III: R1′=H) (1.85 mL, 0.020 mol) and conc. HCl (0.17 mL, 0.02 mol) in 1:1 water/2-methoxyethanol (40 mL) was refluxed for 18 hours, then concentrated to dryness. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic portion was worked up to give an oil which was chromatographed on silica gel. Petroleum ether eluted foreruns, while EtOAc/petroleum ether (1:1) gave 4-(N-phenylamino)-3-nitropyridine (VI: R′=4-aza, R1′=H) (2.02 g, 41%); mp (EtOAc/petroleum ether) 119° C.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customto give an oil which
  4. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-f68ab46a5d9140f78d1f23f6872d12d5
Source dataset
uspto-grants-2001_04
Patent number
US06218388B1

Reaction notes

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