7-(4-(benzyloxy)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one → 7-(4-Hydroxybutoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1750075Notes

Reaction equation

HRID 1750075 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 666339287-(4-(benzyloxy)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 210738467-(4-Hydroxybutoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-oneYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To the solution of intermediate 10 (900 mg, 2.8 mmol) in EtOH (25 mL) was added 10% Pd/C (400 mg) under an atmosphere of H2 overnight. The reaction was filtered to remove the Pd/C and the filtrate was concentrated and washed with Et2O to give 7-(4-hydroxybutoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (intermediate 11) (360 mg, 55%) as a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the Pd/C
  3. concentrationthe filtrate was concentrated
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-18ab8a7b8833454aade4c26209ca03e5
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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