6-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone → 6-[3-(1-Cyclohexyl-1H-tetrazol-5-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one

HRID 1277423Notes

Reaction equation

HRID 1277423 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 130210946-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

Product 1

HCID 129412676-[3-(1-Cyclohexyl-1H-tetrazol-5-yl)propoxy]-3,4-dihydroquinolin-2(1H)-oneYield 59.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into 500 ml of methanol, 2.5 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril is added, then 0.1 of palladium black is added into the mixture and the reaction is carried out under 2.5 atoms of H2 -pressure at 50° C. for 8 hours. After the reaction is completed, the catalyst is removed by filtration and the filtrate is concentrated to dryness. The residue is recrystallized from chloroform-petroleum ether to obtain 1.5 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. Melting point: 154.4°-155.5° C.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe residue is recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-606c5bec8eb840258d0523f7df320aa9
Source dataset
uspto-grants-1981_07
Patent number
US04277479

Reaction notes

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