Potassium Cyanide → 6-(5-Cyano-2-pyridyloxy)-beta-carboline-3-carboxylic Acid Methyl Ester

HRID 2352567노트

반응식

HRID 2352567 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18][C:19]1[CH:24]=[CH:23][C:22](N)=[CH:21][N:20]=1)=[CH:12][CH:11]=3)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[Cu][C:33]#[N:34].[C-]#N.[K+]>O.Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:33]#[N:34])=[CH:21][N:20]=1)=[CH:12][CH:11]=3)=[O:4]

참가 물질

7

반응물 4

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 54171784HCID 54171784, 화합물HCID 178418546HCID 178418546, 화합물

생성물 1

HCID 140719926-(5-Cyano-2-pyridyloxy)-beta-carboline-3-carboxylic Acid Methyl Ester

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매3회

실험 절차

A suspension of 1.7 g of amino derivative (Example 24) in 10 ml of water and 2.5 ml of hydrochloric acid (37%) is combined dropwise at -5° C. with a solution of 0.4 g of NaN2 in 1.5 ml of water, then stirred for another hour at 0°-5° C. By adding sodium carbonate, solution is then adjusted to pH 5.5-6 and poured into a mixture, preheated to about 60° C., of 0.5 g of copper (I) cyanide and 1.6 g of potassium cyanide in 10 ml of water. After the reaction is completed, the cooled-off solution is extracted with dichloromethane, the organic phase is washed with water and concentrated. The residue is purified over silica gel, thus obtaining 1.12 g (65%).

후처리

  1. additionpoured into a mixture
  2. extractionthe cooled-off solution is extracted with dichloromethane
  3. washthe organic phase is washed with water
  4. concentrationconcentrated
  5. customThe residue is purified over silica gel
  6. customthus obtaining 1.12 g (65%)

출처 및 근거

ORD 기록
ord-b366f147969541c4a78a45edc066719e
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04877792

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