Sodium Hydroxide → HCID 135833425, compound

HRID 247128Notes

Reaction equation

HRID 247128 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:39])=[C:5]([C:32]([O:34]CCC#N)=[O:33])[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:7]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][N:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:15])[N:9]=1.[OH-].[Na+]>COCCOC.O>[CH3:1][C:2]1[NH:3][C:4]([CH3:39])=[C:5]([C:32]([OH:34])=[O:33])[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:7]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][N:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:15])[N:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 135833432HCID 135833432, compound

Product 1

HCID 135833425HCID 135833425, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 1.06 g of 2-cyanoethyl 1,4-dihydro-2,6-dimetyl-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-4-(3-nitrophenyl)pyridine-5-carboxylate in 5 ml of ethylene glycol dimethyl ether was added a solution of 240 mg of sodium hydroxide in 10 ml of water. The reaction mixture was stirred at room temperature for 7 hours and then diluted by adding 5 ml of water. The mixture was washed with three 20 ml portions of methylene chloride and then acidified with dilute hydrochloric acid until the pH of the solution was about 1. The solution was decanted and the oily precipitate was dissolved in isopropyl alcohol. After the organic phase was concentrated in vacuo, the residue was chromatographed on silica gel using chloroform-isopropyl alcohol (10:1) as eluent to give 0.715 g of 1,4-dihydro-2,6-dimethyl-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-4-(3-nitrophenyl)pyridine-5-carboxylic acid as an amorphous solid. Recrystallization from ethyl acetate-isopropyl ether gave colorless crystals, m.p. 171° C. (decomp.)

Workup

  1. additiondiluted
  2. washThe mixture was washed with three 20 ml portions of methylene chloride
  3. customThe solution was decanted
  4. dissolutionthe oily precipitate was dissolved in isopropyl alcohol
  5. concentrationAfter the organic phase was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-132aa8010d78426c9f1c1fd0e77a3373
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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