Sodium hydride → HCID 13240342, compound

HRID 1649593Notes

Reaction equation

HRID 1649593 reaction equation
[H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([C:12]3[N:13]=[N:14][C:15](=[O:17])[CH:16]=3)=[CH:6][C:5]=2[O:4]1.[H][H].S(O[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([C:40]1[CH:41]([C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([N+:58]([O-:60])=[O:59])[CH:53]=2)[C:42]([C:48]([O:50][CH3:51])=[O:49])=[C:43]([CH3:47])[NH:44][C:45]=1[CH3:46])=[O:39])(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([C:12]3[NH:13][N:14]=[C:15]([O:17][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([C:40]4[CH:41]([C:52]5[CH:57]=[CH:56][CH:55]=[C:54]([N+:58]([O-:60])=[O:59])[CH:53]=5)[C:42]([C:48]([O:50][CH3:51])=[O:49])=[C:43]([CH3:47])[NH:44][C:45]=4[CH3:46])=[O:39])[CH:16]=3)=[CH:6][C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 13245578HCID 13245578, compoundHCID 53775369HCID 53775369, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13240342HCID 13240342, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.24 g (10 mmole) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide, to which was added 2.45 g (12 mmole) of 3-(3,4-methylenedioxyphenyl)-5-pyrazolone with stirring at room temperature. After evolution of hydrogen had ceased, to this solution was added dropwise 10 ml of a solution of 5.87 g (10 mmole) of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-tosyloxyhexyl ester in N,N-dimethylformamide, and the mixture was stirred and heated at 90° C. for an hour. The resultant reaction mixture was poured into 200 ml of ice water, and the separated solid was filtered off. This solid was recrystallized from ethyl acetate to obtain 3.21 g (yield 51.9%) of the 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-methoxycarbonylpyridine-5-carboxylic acid 6-[5-(3,4-methylenedioxyphenyl)-3-pyrazolyloxy]hexyl ester.

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated at 90° C. for an hour
  3. customThe resultant reaction mixture
  4. filtrationthe separated solid was filtered off
  5. customThis solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ffc755195b3240b08bb2a1366c847ac9
Source dataset
uspto-grants-1983_11
Patent number
US04418197

Reaction notes

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