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

HRID 1085142Notes

Reaction equation

HRID 1085142 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>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

5

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 1

HCID 702EthanolSolvent

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 (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. customfor 3.5 hours
  2. filtrationThe catalyst was filtered off
  3. customthe solvent removed under reduced pressure
  4. customto give a brown solid, (1.8 g) which

Sources & evidence

ORD record
ord-dcab92b0be194c97bc5a58c550845c4c
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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