Sodium Bicarbonate → 2,7-Dimethoxy-1,5-naphthyridine

HRID 656876ノート

反応式

HRID 656876 の反応式
Br[C:2]1[C:3]([O:14][CH3:15])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.C(=O)([O-])O.[Na+].[H][H]>CO.[Pd]>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:2][C:3]([O:14][CH3:15])=[CH:4][N:5]=2)[N:10]=1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 585793648-Bromo-2,7-dimethoxy-1,5-naphthyridineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 585794032,7-Dimethoxy-1,5-naphthyridine収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

8-Bromo-2,7-bis(methoxy)-1,5-naphthyridine (11.21 g, 41.673 mmol) was stirred in MeOH (400 mL) with sodium hydrogen carbonate (7.00 g, 83.35 mmol) and 10% palladium on carbon (2.8 g), and the resulting suspension was hydrogenated at 1 atmosphere of hydrogen pressure for 18 h. The mixture was filtered with suction through celite and the solids were washed with ethanol (300 ml). The filtrate was concentrated under reduced pressure and the residue treated with DCM (300 ml) and water (300 ml). The aqueous phase was extracted with DCM (2×300 ml). The combined organic phases were separated, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give 2,7-bis(methoxy)-1,5-naphthyridine as a cream solid (7.45 g, 94%).

後処理

  1. filtrationThe mixture was filtered with suction through celite
  2. washthe solids were washed with ethanol (300 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthe residue treated with DCM (300 ml) and water (300 ml)
  5. extractionThe aqueous phase was extracted with DCM (2×300 ml)
  6. customThe combined organic phases were separated
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-8a233f64e8ec470896436e56b69f4f34
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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