Ethyl levulinate → trans-6-Cyano-4-(I,6-dihydro-3-methyl-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-ol

HRID 1974839

Reaction equation

HRID 1974839 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH:7]1[O:15][CH:6]21)#[N:2].[CH3:16][C:17]1[CH:18]=[CH:19][C:20](=[O:23])[NH:21][N:22]=1.C(OCC)(=O)CCC(C)=O.O.NN.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]2[N:21]1[C:20](=[O:23])[CH:19]=[CH:18][C:17]([CH3:16])=[N:22]1)#[N:2]

Participants

8

Reactant 5

HCID 10883Ethyl levulinateHCID 24654Hydrazine hydrate (1:1)HCID 66854Benzyltrimethylammonium hydroxideHCID 833466-methylpyridazin-3(2H)-oneHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 67823752trans-6-Cyano-4-(I,6-dihydro-3-methyl-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-olYield 38.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture is prepared which contains 1 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane and 1.1 g of 6-methylpyridazin-3-one (prepared by the method described in J. Chem. Soc., 1947, p. 241, by reacting ethyl levulinate with hydrazine hydrate) in 10 ml of dioxane containing 0.1 ml of a 35% methanolic solution of benzyltrimethylammonium hydroxide. After 2 days at room temperature, the mixture is diluted with water and filtered, the material on the filter is dissolved in ethyl acetate, the water is then decanted and the organic phase is dried and concentrated. After recrystallization from an ethyl acetate/isopropyl ether mixture, 0.6 g of the expected product is obtained.

Workup

  1. customA mixture is prepared which
  2. customprepared by the method
  3. filtrationfiltered
  4. dissolutionthe material on the filter is dissolved in ethyl acetate
  5. customthe water is then decanted
  6. customthe organic phase is dried
  7. concentrationconcentrated
  8. customAfter recrystallization from an ethyl acetate/isopropyl ether mixture

Sources & evidence

ORD record
ord-b77f316b6fdf4118aa48e5154e6ea792
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Linked notes

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