Sodium Hydroxide → HCID 18956132, compound

HRID 2379702Notes

Reaction equation

HRID 2379702 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O1CCOCC1.[Pd]>[CH3:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:2]=[C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[N:4]=[N:5]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20077492HCID 20077492, compound

Product 1

HCID 18956132HCID 18956132, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

12 g (47.2 mmol) of the compound from Example VII are hydrogenated for several hours at 3 bar in the Parr apparatus in 400 ml of dioxane and 75 ml of 1N NaOH in the presence of 1.5 g of Pd-C (5% strength) with TLC checking. Solid is then filtered off with suction through kieselguhr and the filtrate is concentrated on a rotary evaporator. After chromatography on silica gel (toluene→toluene/ethyl acetate 1:1), 1.8 g (17%) of the pure title compound are obtained. M.p.: 101° C.

Workup

  1. filtrationSolid is then filtered off with suction through kieselguhr
  2. concentrationthe filtrate is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-b39480407fd44eceb0cc4a2a932ee44c
Source dataset
uspto-grants-1994_11
Patent number
US05364855

Reaction notes

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