Ethanol → HCID 178419876, compound

HRID 1077042Notes

Reaction equation

HRID 1077042 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[C:9]3[C:12]4[C:17]([CH2:18][CH2:19][C:8]=23)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:3][CH:2]=1.C(O)C.O1CCOCC1>[Pd].CO.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[C:9]3[C:12]4[C:17]([CH:18]=[CH:19][C:8]=23)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 312751,4-DioxaneHCID 178419874HCID 178419874, compound

Product 1

HCID 178419876HCID 178419876, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 6.0 grams of 4,5-dihydro-3-(4-pyridyl)-2H-naphtho [1,2-c]pyrazole, 6.0 grams of 5% palladium or carbon, 150 ml of absolute ethanol and 50 ml of dry dioxane are stired and refluxed for about 75 hours. The mixture is allowed to cool to room temperature, and is then treated with about 50 ml of 1:1 methanol/methylene dichloride. The mixture is stirred for about 15 minutes and then filtered through celite. The filtrate is concentrated in vacuo and the residue crystallized from ethanol/ether to give 3-(4-pyridyl)-2H-naphtho[1,2-c]pyrazole, (m.p. 273°-276°.)

Workup

  1. temperaturerefluxed for about 75 hours
  2. filtrationfiltered through celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe residue crystallized from ethanol/ether

Sources & evidence

ORD record
ord-bd96e8b12d484b9e9c8c64239e40ab7e
Source dataset
uspto-grants-1976_05
Patent number
US03959308

Reaction notes

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