HCID 21392597, compound → HCID 21392593, compound

HRID 1580712Notes

Reaction equation

HRID 1580712 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([C:14]3[N:18]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[N:16][N:15]=3)=[CH:10][C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]>[Pd].C(O)C>[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:28][O:27][C:7]1[C:8]2[C:9](=[O:26])[CH:10]=[C:11]([C:14]3[N:18]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[N:16][N:15]=3)[O:12][C:13]=2[C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 21392597HCID 21392597, compound

Product 1

HCID 21392593HCID 21392593, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.34 parts of 5-[8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-yl]-N-benzyltetrazole in 1000 parts of ethanol was hydrogenated at room temperature and pressure for 20 hours using 0.14 parts of 5% palladium on charcoal as catalyst. The reaction mixture was filtered and the solvent removed by evaporation. Crystallisation of the residue from chloroform/light petroleum (40:60) gave 1.89 parts of 5-[5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-yl]-N-benzyltetrazole, m.p. 87°-87.5°C.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed by evaporation
  4. customCrystallisation of the residue from chloroform/light petroleum (40:60)

Sources & evidence

ORD record
ord-39521644456042a19e27b17d4601aa46
Source dataset
uspto-grants-1976_01
Patent number
US03933845

Reaction notes

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