Sodium Hydroxide → 3'-Fluoro-5,6'-dimethyl-2,2'-bipyridin-4-amine

HRID 1522573Notes

Reaction equation

HRID 1522573 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([CH3:18])=[CH:11][N+:10]=2[O-])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[OH-].[Na+]>CC(O)=O.[Fe]>[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([CH3:18])=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 674695932-(3-Fluoro-6-methylpyridin-2-yl)-5-methyl-4-nitropyridine 1-oxide

Product 1

HCID 674696193'-Fluoro-5,6'-dimethyl-2,2'-bipyridin-4-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-fluoro-6-methylpyridin-2-yl)-5-methyl-4-nitropyridine 1-oxide (2.7 g, 10.2 mmol) in AcOH (54 mL) was added iron (2.3 g, 40.9 mmol) and the mixture was stirred at 100° C. for 30 minutes, cooled to room temperature, adjusted pH to about 8 with NaOH (1N) and extracted with ethyl acetate. The organic layers were concentrated to give 3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-amine. 1HNMR (CDCL3) δ ppm 8.32 (s, 1H), 7.43-7.38 (m, 1H), 7.19-7.15 (m, 2H), 4.19 (s, 2H), 2.65 (s, 3H), 2.19 (s, 3H). MS [M+H] found 218.0.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layers were concentrated

Sources & evidence

ORD record
ord-6387fea554e945f792bd166ea1b11fe8
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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