Acetic Acid → HCID 22724440, compound

HRID 2086795Notes

Reaction equation

HRID 2086795 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:18]2[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][CH:16]=1.C(O)(=O)C>C(O)C.C(Cl)(Cl)Cl.[Fe]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 227244452-[3-(2-Naphthyl)phenylamino]-3-nitropyridine

Product 1

HCID 22724440HCID 22724440, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-[3-(2-naphthyl)phenylamino]-3-nitropyridine (3.0 g), iron (2.46 g) and acetic acid (5.28 g) in ethanol (14 ml) was stirred under reflux for 6 hours. The reaction mixture was diluted with chloroform, filtered and treated with saturated sodium bicarbonate solution. The chloroform layer was separated, dried, evaporated and chromatographed on silica gel to give 2-[3-(2-naphthyl)phenylamino]-3-aminopyridine (1.2 g, 43.9%).

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationfiltered
  3. additiontreated with saturated sodium bicarbonate solution
  4. customThe chloroform layer was separated
  5. customdried
  6. customevaporated
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-f55bcfce1e1a4e26b292df4e99fcbb99
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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