1,6-Naphthyridine → HCID 12783992、化合物

HRID 1660499

反応式

HRID 1660499 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1O[C:14]([CH2:16][CH2:17][CH2:18][CH2:19]Br)([CH3:15])[O:13]C1.[BH4-].[Na+]>C(#N)C>[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][CH2:16][C:14](=[O:13])[CH3:15]

参加物

5

反応物 3

HCID 674881,6-NaphthyridineHCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolaneHCID 4311764Sodium borohydride

生成物 1

HCID 12783992HCID 12783992、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1,6-naphthyridine (13.0 g, 0.1 mol) and 6-bromohexan-2-one ethylene ketal (26.8 g, 0.12 mol) in acetonitrile (100 ml) was refluxed for 10 hours. The reaction mixture was evaporated in vacuo, dissolved in methanol (600 ml) and water (200 ml). To the mixture, sodium borohydride (19.5 g, 0.5 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 ethyl acetate. The organic layer was dried over anhydrous potassium carbonate, evaporated in vacuo. The resulting residue was dissolved in 1 N-HCl and stirred overnight, neutralized with 33% NaOH solution and extracted with chloroform. The organic layer was dried over anhydrous potassium carbonate, evaporated in vacuo. The residue was purified by alumina column chromatography (eluted with chloroform-methanol (10:1)) and distilled, bp. 157°-158° C./0.6 mmHg, to afford the Compound No. 29 (9.3 g, 40.1%) as a light yellow oil.

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutiondissolved in methanol (600 ml)
  3. customrange 0° to 20° C
  4. customthe reaction mixture was evaporated in vacuo, water
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  8. customevaporated in vacuo
  9. dissolutionThe resulting residue was dissolved in 1 N-HCl
  10. stirringstirred overnight
  11. extractionextracted with chloroform
  12. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  13. customevaporated in vacuo
  14. customThe residue was purified by alumina column chromatography (eluted with chloroform-methanol (10:1))
  15. distillationdistilled
  16. custombp. 157°-158° C./0.6 mmHg, to afford the Compound No

出典と根拠

ORDレコード
ord-48cb9bbed8f54fbd8e794c8cb1e9dc02
出典データセット
uspto-grants-1981_12
特許番号
US04308273

関連ノート

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