Sodium Hydroxide → 2-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde

HRID 906332Notes

Reaction equation

HRID 906332 reaction equation
[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[C:13]([C:14]#N)=[CH:12][CH:11]=[C:10]([CH2:16][CH3:17])[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.[OH-:30].[Na+]>ClCCl>[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[N:9]=[C:10]([CH2:16][CH3:17])[CH:11]=[CH:12][C:13]=2[CH:14]=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21225700Diisobutylaluminumhydride2×HCID 673913322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile

Product 1

HCID 866284322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehydeYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile (484 mg, 1.87 mmol) in dichloromethane (5 mL) was added with diisobutylaluminum hydride (0.99 M solution in toluene, 1.99 mL, 1.97 mmol) at −78° C., and the mixture was stirred at the same temperature for 4 hours. The mixture was further added with diisobutylaluminum hydride (0.99 M solution in toluene, 0.2 mL, 0.198 mmol) at the same temperature, and the mixture was stirred at the same temperature for 45 minutes. Then, the mixture was added with 2 M aqueous sodium hydroxide, stirred at room temperature for 30 minutes, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde (233 mg, 48%) as yellow oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 45 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-a0a1fb7b69994a9cb939575a14430774
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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