1,6-Naphthyridine → HCID 12783984, compound

HRID 1660498Notes

Reaction equation

HRID 1660498 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.S(C1C=CC(C)=CC=1)(O[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])(=O)=O.[BH4-].[Na+]>CO.O>[CH2:19]([N:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)[CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 674881,6-NaphthyridineHCID 4311764Sodium borohydrideHCID 11064521HCID 11064521, compound

Product 1

HCID 12783984HCID 12783984, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,6-naphthyridine (6.5 g, 0.05 mol) and 4-pentenyl tosylate was heated at 80° C. for 6 hours. The reaction mixture was dissolved in methanol (300 ml) and water (100 ml). To the mixture, sodium borohydride (9.5 g, 0.25 mol) was added portionwise over the internal temperature range 0° to 20° C. After stirring overnight at room temperature, the reaction mixture was evaporated in vacuo, water added and extracted with ether. The organic layer was dried over anhydrous potassium carbonate and evaporated in vacuo. The resulting residue was purified by alumina column chromatography (eluted successively with petroleum ether and ether) and distilled, bp. 110°-112° C./0.35 mmHg, to afford the Compound No. 15 (6.9 g, 68.6%) as a colorless oil.

Workup

  1. customrange 0° to 20° C
  2. customthe reaction mixture was evaporated in vacuo, water
  3. additionadded
  4. extractionextracted with ether
  5. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by alumina column chromatography (
  8. washeluted successively with petroleum ether and ether) and
  9. distillationdistilled
  10. custombp. 110°-112° C./0.35 mmHg, to afford the Compound No

Sources & evidence

ORD record
ord-f3a993643489413888398e0e94e911b0
Source dataset
uspto-grants-1981_12
Patent number
US04308273

Reaction notes

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