HCID 21392593, compound → HCID 178439276, compound

HRID 461833Notes

Reaction equation

HRID 461833 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[O:28])[CH:13]=[C:14]([C:16]3[N:20](CC4C=CC=CC=4)[N:19]=[N:18][N:17]=3)[O:15][C:10]=2[C:9]([CH2:29][CH2:30][CH3:31])=[CH:8][CH:7]=1.[H][H]>[Pd].C(O)C>[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[O:28])[CH:13]=[C:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[O:15][C:10]=2[C:9]([CH2:29][CH2:30][CH3:31])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 21392593HCID 21392593, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178439276HCID 178439276, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.96 parts of 5-[5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-yl]-N-benzyltetrazole in 500 parts of ethanol was stirred at 60° C, with 0.096 parts of 5% palladium on charcoal, in an atmosphere of hydrogen for 11 1/2 hours. The reaction mixture was cooled, was filtered and the solvent removed by evaporation to give a residue which was chromatographed on silica gel. Careful elution with chloroform and chloroform/acetone gave 0.16 parts of 5-[5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-yl]tetrazole, m.p. 199°-200° C (after recrystallisation from ethanol).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationwas filtered
  3. customthe solvent removed by evaporation
  4. customto give a residue which
  5. customwas chromatographed on silica gel
  6. washCareful elution with chloroform and chloroform/acetone
  7. customgave
  8. custom0.16 parts of 5-[5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-yl]tetrazole, m.p. 199°-200° C (after recrystallisation from ethanol)

Sources & evidence

ORD record
ord-112e2ab422a744bfa52c24e8154635da
Source dataset
uspto-grants-1977_12
Patent number
US04064256

Reaction notes

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