Dichloromethane → 4-(4-Acetylphenyl)amino-3-aminopyridine

HRID 6353Notes

Reaction equation

HRID 6353 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-])=O)=[CH:7][CH:6]=1)(=[O:4])[CH3:3].[OH-].[Na+].ClCCl>[Pd].C(O)C>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH2:18])=[CH:9][CH:10]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 197912824-(4-Acetylphenyl)amino-3-nitropyridine hydrochloride

Product 1

HCID 197912814-(4-Acetylphenyl)amino-3-aminopyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

4-(4-Acetylphenyl)amino-3-nitropyridine hydrochloride (2.0 g, 71.8 mmol) was partitioned between aqueous sodium hydroxide and dichloromethane (3×20 ml). The combined organic phases were washed with water (20 ml) and concentrated under reduced pressure to give a solid. Ethanol (20 ml) was added, and the solution was hydrogenated over 5% palladium on carbon (0.2 g) at 50 p.s.i. (345 kPa) for 3.5 hours. The catalyst was filtered off, and the solvent removed under reduced pressure to give a brown solid, (1.8 g) which was used directly for the next reaction without purification, m.p. 165°-166° C. (after recrystallisation from ethanol).

Workup

  1. washThe combined organic phases were washed with water (20 ml)
  2. concentrationconcentrated under reduced pressure
  3. customto give a solid
  4. filtrationThe catalyst was filtered off
  5. customthe solvent removed under reduced pressure
  6. customto give a brown solid, (1.8 g) which

Sources & evidence

ORD record
ord-8a022d8b3e334c6db46c27f865df462d
Source dataset
uspto-grants-1993_09
Patent number
US05248681

Reaction notes

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