Stannous chloride dihydrate → 3-Amino-4-[N-(4-cyanophenyl)amino]pyridine

HRID 249253Notes

Reaction equation

HRID 249253 reaction equation
O.O.[Sn](Cl)Cl.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N+:21]([O-])=O)=[CH:10][CH:9]=1)#[N:7]>Cl.O.C(O)C>[NH2:21][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[NH:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]#[N:7])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 105620064-[N-(4-Cyanophenyl)amino]-3-nitropyridine

Product 1

HCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridineYield 88.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to a modification of the method of Pharm. Helv. Acta, 50, 188 (1975), tin(II) dichloride dihydrate (56.4 g, 250 mmol) was added to a suspension of 4-[N-(4-cyanophenyl)amino]-3-nitropyridine (see part (a)) (12.0 g, 50 mmol) in 2N aqueous hydrochloric acid (35 ml), water (150 ml) and ethanol (75 ml) and the resulting mixture was heated under reflux for 10 minutes under nitrogen. The mixture was cooled in ice, poured into ice-cold 2N aqueous sodium hydroxide (400 ml) and filtered The creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water, and then dried in a vacuum desiccator to provide the title compound, (9.31 g), which gradually turns reddish brown on exposure to light and air.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 10 minutes under nitrogen
  3. temperatureThe mixture was cooled in ice
  4. filtrationfiltered The creamy-coloured solid
  5. washwas washed with 2N aqueous sodium hydroxide and water
  6. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-8ebbe19c6c674bb89f5d18a62cfc96ff
Source dataset
uspto-grants-1993_05
Patent number
US05214044

Reaction notes

Loading…