HCID 19815963, compound → HCID 19815891, compound

HRID 2247879Notes

Reaction equation

HRID 2247879 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2[C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2[C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 19815963HCID 19815963, compound

Product 1

HCID 19815891HCID 19815891, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(5-hydroxymethyl-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (4.4 g) and activated manganese dioxide (26 g) in ethyl acetate (100 ml) was refluxed for 3 hours under stirring. Manganese dioxide was filtered off and the filtrate was evaporated in vacuo and the residue was subjected to column chromatography on silica gel. The column was eluted with a mixture of ethyl acetate and tetrahydrofuran (7:3 V/V) and the fraction was evaporated in vacuo. The residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to give 4-(5-formyl-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (1.2 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationManganese dioxide was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. washThe column was eluted with a mixture of ethyl acetate and tetrahydrofuran (7:3 V/V)
  5. customthe fraction was evaporated in vacuo
  6. customThe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-baf6e744a5da44dba9ea90c821dec7d6
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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