HCID 178446915, compound → HCID 178446909, compound

HRID 461828Notes

Reaction equation

HRID 461828 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[O:21])[CH:13]=[C:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[O:15][C:10]=2[CH:9]=[CH:8][CH:7]=1>[Ni].C(O)C>[CH3:1][CH:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[O:21])[CH2:13][CH:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[O:15][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 178446915HCID 178446915, compound

Product 1

HCID 178446909HCID 178446909, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1 part of 5-[5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-yl]tetrazole in 50 parts of ethanol was added 5 parts of Raney nickel catalyst. The resulting mixture was hydrogenated at 20° C and 45 lbs/sq. in. pressure for 8 hours. The catalyst was filtered off and the filtrate was evaporated to give an oil which solidified on trituration with petroleum ether (b.p. 40°-60° C). This solid was crystallised from a mixture of ethyl acetate and petroluem ether (b.p. 40°-60° C) to give 0.2 parts of 5-[2,3-dihydro-5-(3-methylbutoxy)-4-oxo-4H-1-benzopyran-2-yl] tetrazole as a white solid, m.p. 134°-137° C. The structure of this product was confirmed by n.m.r. and m.s. measurements.

Workup

  1. customwas hydrogenated at 20° C
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated
  4. customto give an oil which
  5. customThis solid was crystallised from a mixture of ethyl acetate and petroluem ether (b.p. 40°-60° C)

Sources & evidence

ORD record
ord-c5d4419e0db446e6be0dc0c46570e4d9
Source dataset
uspto-grants-1977_12
Patent number
US04064256

Reaction notes

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