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Acetic Acid → 4-Methyl-beta-carbolin-3,6-dicarboxylic acid dimethyl ester

HRID 1757985
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인쇄 미리보기

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HRID 1757985 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([C:20]#N)=[CH:13][CH:12]=3)=[O:5])C.[OH-:22].[K+].[C:24](O)(=[O:26])C>C(O)CO.O>[CH3:1][O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([C:20]([O:26][CH3:24])=[O:22])=[CH:13][CH:12]=3)=[O:5]
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참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 130373416-Cyano-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

생성물 1

HCID 130373564-Methyl-beta-carbolin-3,6-dicarboxylic acid dimethyl ester

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water
용매

반응 조건

온도
0 °C

실험 절차

2.81 g of 6-cyano-4-methyl-β-carbolin-3-carboxylic acid ethyl ester is heated with 4.6 g of potassium hydroxide in 20 ml of ethylene glycol for 16 hours at 150° C. After cooling to 0° C., 10 ml of acetic acid is added dropwise. The mixture is diluted with 100 ml of water and, after saturation with sodium chloride, is extracted with ethyl acetate. The extracts are washed until neutral with saturated common salt solution, dried using sodium sulphate, filtered, and the solvent is distilled off in vacuo. The crude product is dissolved in 30 ml of 10% methanolic hydrochloric acid and boiled for 5 hours under reflux. After distilling off the solvent in vacuo, 20 ml of dilute aqueous ammonia are added and the mixture is extracted with ethyl acetate. After washing until neutral, drying and distilling off the solvent, the crude product is recrystallized from diisopropyl ether. 1.36 g of 4-methyl-β-carbolin-3,6-dicarboxylic acid dimethyl ester of melting point 199°-204° C. is obtained.

후처리

  1. extractionafter saturation with sodium chloride, is extracted with ethyl acetate
  2. washThe extracts are washed until neutral with saturated common salt solution
  3. customdried
  4. filtrationfiltered
  5. distillationthe solvent is distilled off in vacuo
  6. dissolutionThe crude product is dissolved in 30 ml of 10% methanolic hydrochloric acid
  7. temperatureunder reflux
  8. distillationAfter distilling off the solvent in vacuo, 20 ml of dilute aqueous ammonia
  9. additionare added
  10. extractionthe mixture is extracted with ethyl acetate
  11. washAfter washing until neutral,
  12. customdrying
  13. distillationdistilling off the solvent
  14. customthe crude product is recrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-d4e57a5bfab649438ce37243fa16d308
출처 데이터셋
uspto-grants-1983_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04371536

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