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

HRID 396693Notes

Reaction equation

HRID 396693 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:9][C:10]([CH3:34])=[C:11]([C:30]([O:32][CH3:33])=[O:31])[CH:12]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:13]=1[C:14]([O:16]CCC#N)=[O:15])=[N+:2]=[N-:3].[OH-].[K+]>CC(C)=O>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:9][C:10]([CH3:34])=[C:11]([C:30]([O:32][CH3:33])=[O:31])[CH:12]([C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[C:13]=1[C:14]([OH:16])=[O:15])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 865866352-(4-Azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine

Product 1

HCID 183607782-(4-Azidobutyl)-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine-3-carboxylic acidYield 61.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-(4-azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine (1.38 g,. 2.95 mmol) in 10 ml acetone was treated with 15 ml 1N 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 750 mg (61% yield) of 2-(4-azidobutyl)-1,4-dihydro-5-methoxycarbonyl-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-89cc6abd8498417b9c5d56464eeba32f
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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