Potassium Hydroxide → 5-Acetyl-2-(4-azidobutyl)-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine-3-carboxylic acid

HRID 396701Notes

Reaction equation

HRID 396701 reaction equation
[C:1]([C:4]1[CH:5]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[C:6]([C:18]([O:20]CCC#N)=[O:19])=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[OH-].[K+]>CC(C)=O>[C:1]([C:4]1[CH:5]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[C:6]([C:18]([OH:20])=[O:19])=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 230040535-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine

Product 1

HCID 230041805-Acetyl-2-(4-azidobutyl)-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine-3-carboxylic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine (1.05 g, 2.32 mmol) in 10 ml of acetone was treated with 20 ml of 1N aqueous KOH solution at 0° C. for 1 hr. The acetone was removed in vacuo and the aqueous layer was acidified to pH=3 by 2N hydrochloric acid, the resulting yellow precipitate was collected by filtration, washed with 10 ml of cold water and dried in vacuo to yield 0.60 g (60% yield) of 5-acetyl-2-(4-azidobuyl)-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine-3-carboxylic acid as a yellow powder.

Workup

  1. customThe acetone was removed in vacuo
  2. filtrationthe resulting yellow precipitate was collected by filtration
  3. washwashed with 10 ml of cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-acc7df59c2c044ce80a192f3ec65a2ea
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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