Ethanol → HCID 19363364, compound

HRID 850509Notes

Reaction equation

HRID 850509 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:11]2[C:6]([C:7](=[O:31])[N:8]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=3)[C:9](=[O:19])[NH:10]2)=[CH:5][CH:4]=1.C(O)C.[H][H]>[C].[Pd].O1CCOCC1>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][N:8]2[C:7](=[O:31])[C:6]3[C:11](=[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:10][C:9]2=[O:19])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 19363223HCID 19363223, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363364HCID 19363364, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

7-Methoxy-3-[2-(4-nitrophenyl)ethyl]-8-pentyloxy-1H-quinazoline-2,4-dione (45.0 g, 105 mmol) obtained in Example 7-39, ethanol (1300 ml) and dioxane (700 ml) were mixed, and 10% palladium-carbon catalyst (4.5 g) was added to this solution. The reaction mixture was stirred in a stream of hydrogen at room temperature for 16.5 hours, followed by filtration. Activated charcoal (2.6 g was added to the filtrate, and the reaction mixture was stirred at 50° C. for 1 hour and then filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=3/1). The precipitated crude crystals were recrystallized from ethanol-hexane to give 3-[2-(4-aminophenyl)ethyl]-7-methoxy-8-pentyloxy-1H-quinazoline-2,4-dione (33.82 g, 81%) as pale-yellow crystals.

Workup

  1. filtrationfollowed by filtration
  2. additionActivated charcoal (2.6 g was added to the filtrate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=3/1)
  6. customThe precipitated crude crystals
  7. customwere recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-b4f88f0a8f42411c94f7263418bf36b5
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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