Diethyl Ether → 4-Amino-1-Isobutyl-1,2-Dihydro-2-Oxo-1,8-Naphthyridine-3-Carboxylic Acid Ethyl Ester

HRID 2285820

반응식

HRID 2285820 반응식
[CH2:1]([NH:5][C:6]1[N:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9])[CH:2]([CH3:4])[CH3:3].C([CH:16]([C:20](Cl)=[O:21])[C:17](Cl)=[O:18])C.[CH2:23]([O:25]CC)[CH3:24]>>[CH2:23]([O:25][C:20]([C:16]1[C:17](=[O:18])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]2[C:7]([C:8]=1[NH2:9])=[CH:10][CH:11]=[CH:12][N:13]=2)=[O:21])[CH3:24]

참가 물질

4

반응물 3

HCID 3283Diethyl EtherHCID 109209242-Ethylpropanedioyl dichlorideHCID 128186522-(Isobutylamino)nicotinonitrile

생성물 1

HCID 128186194-Amino-1-Isobutyl-1,2-Dihydro-2-Oxo-1,8-Naphthyridine-3-Carboxylic Acid Ethyl Ester

실험 절차

To a solution of 12.25 g. (0.07 mole) of 2-isobutylaminonicotinonitrile in 300 ml. of anhydrous ethyl ether was added 5.2 g. (0.035 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 30 minutes and was filtered. The filtrate was evaporated in a rotary evaporator and the residue was dissolved in 20 ml. of ethanol. This solution was added to a solution of 1.6 g. of sodium in 150 ml. of ethanol. After stirring at room temperature for 5 minutes, the mixture was diluted with water and was acidified with conc. hydrochloric acid. The precipitate which formed was collected, air dried and was recrystallized from ethyl acetate to afford 2.1 g. of the title product, m.p. 157°-159° C.

후처리

  1. filtrationwas filtered
  2. customThe filtrate was evaporated in a rotary evaporator
  3. dissolutionthe residue was dissolved in 20 ml
  4. additionThis solution was added to a solution of 1.6 g
  5. stirringAfter stirring at room temperature for 5 minutes
  6. additionthe mixture was diluted with water
  7. customThe precipitate which formed
  8. customwas collected
  9. customair dried
  10. customwas recrystallized from ethyl acetate
  11. customto afford 2.1 g

출처 및 근거

ORD 기록
ord-7608d10168c54d33b861ea25629893e2
출처 데이터셋
uspto-grants-1982_04
특허 번호
US04324893

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