1,6-Naphthyridine → 1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-((3,4-dimethoxyphenyl)methyl)-

HRID 1660500Notes

Reaction equation

HRID 1660500 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:16]Cl.[BH4-].[Na+]>CO>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:16][N:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6]1

Participants

5

Reactant 3

HCID 674881,6-NaphthyridineHCID 81740Veratryl chlorideHCID 4311764Sodium borohydride

Product 1

HCID 30586961,6-Naphthyridine, 5,6,7,8-tetrahydro-6-((3,4-dimethoxyphenyl)methyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,6-naphthyridine (5.2 g, 0.04 mol) and 3,4-dimethoxybenzyl chloride (8.95 g, 0.048 mol) was refluxed for 3 hours. The precipitated quatenary salt was separated by filtration, dissolved in technical grade methanol (400 ml) and sodium borohydride (15.1 g, 0.4 mol) was added portionwise under ice cooling. After stirring overnight at room temperature, the reaction mixture was evaporated in vacuo, water added and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by alumina column chromatography (eluted successively with n-hexane, benzene and chloroform). The resulting residue was recrystallized from ether-n-hexane to afford the Compound No. 46 (6.5 g, 57.2%) as colorless prisms, mp. 76°-77° C.

Workup

  1. customThe precipitated quatenary salt was separated by filtration
  2. additionwas added portionwise under ice cooling
  3. customthe reaction mixture was evaporated in vacuo, water
  4. additionadded
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by alumina column chromatography (
  9. washeluted successively with n-hexane, benzene and chloroform)
  10. customThe resulting residue was recrystallized from ether-n-hexane
  11. customto afford the Compound No

Sources & evidence

ORD record
ord-987c0100edf244dab9944a0e146afb12
Source dataset
uspto-grants-1981_12
Patent number
US04308273

Reaction notes

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