Sodium Hydroxide → 5-Methyl-3-phenyl-1,7-naphthyridine

HRID 2379699Notes

Reaction equation

HRID 2379699 reaction equation
Cl[C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:5]2.[OH-].[Na+]>C(O)C.[Pd]>[CH3:18][C:3]1[CH:2]=[N:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:7]=[N:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 99925076-Chloro-5-methyl-3-phenyl-1,7-naphthyridine

Product 1

HCID 100821995-Methyl-3-phenyl-1,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

33.7 g (132 mmol) of the compound from Example II are dissolved in 600 ml of ethanol, the solution is treated with 293 ml of 1N NaOH and 10 g of 5% Pd/C and the mixture is immediately hydrogenated in the Parr apparatus at 3 bar for 30 min. It is filtered through kieselguhr and the ethanol content is evaporated in vacuo. The product precipitated in this way is filtered off with suction, washed with plenty of water and then with ether and dried. Yield: 23.6 g (81.2%) M.p.: 135°-138° C.

Workup

  1. filtrationIt is filtered through kieselguhr
  2. customthe ethanol content is evaporated in vacuo
  3. customThe product precipitated in this way
  4. filtrationis filtered off with suction
  5. washwashed with plenty of water
  6. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-8f6e2384660f4980a8609d32a233fcd2
Source dataset
uspto-grants-1994_11
Patent number
US05364855

Reaction notes

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