Sodium Hydroxide → Sodium 6-cyclopentyl-5'-methyl-3,3'-bipyridine-5-carboxylate

HRID 1675947Notes

Reaction equation

HRID 1675947 reaction equation
[CH:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[CH:8][C:7]=2[C:19]([O:21]C)=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+:24]>C1COCC1.CO>[CH:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[CH:8][C:7]=2[C:19]([O-:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5]1.[Na+:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58539038Methyl 6-cyclopentyl-5'-methyl-3,3'-bipyridine-5-carboxylate

Product 1

HCID 67345386Sodium 6-cyclopentyl-5'-methyl-3,3'-bipyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-cyclopentyl-5′-methyl-3,3′-bipyridine-5-carboxylate (6-2, 0.060 g, 0.020 mmol, 1.0 equiv) in THF/methanol (1.7 mL/0.3 mL) was added 10 N sodium hydroxide (0.10 mL, 1.0 mmol, 5.0 equiv) and the system was stirred for 18 h at ambient temperature. The reaction mixture was concentrated and azeotroped with ethyl acetate (2×10 mL) and toluene (3×10 mL) to afford the desired product (6-3) as a white solid. ESI+MS [M+H]+ C17H18N2O2 calc'd 283.1, found 283.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with ethyl acetate (2×10 mL) and toluene (3×10 mL)

Sources & evidence

ORD record
ord-d8417c52a200410aa9a12987aa97e424
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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