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Dimethylformamide → HCID 131716995, 화합물

HRID 727792
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HRID 727792 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[CH:9]([CH2:10][C:11](=[O:21])[N:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[N:13]=3)[CH2:8][CH2:7][C:6]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>O>[ClH:34].[ClH:34].[O:41]1[CH2:42][CH2:43][N:38]([CH2:37][CH2:36][CH2:35][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:14]4[CH:9]([CH2:10][C:11](=[O:21])[N:12]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=5)[N:13]=4)[CH2:8][CH2:7][C:6]=3[CH:22]=2)[CH2:39][CH2:40]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 135816633HCID 135816633, 화합물

생성물 1

HCID 131716995HCID 131716995, 화합물수율 30.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

To a mixture of 1.4 g of 8-hydroxy-2-(2-pyridyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one, 1.4 g of potassium carbonate and 30 ml of dimethylformamide is added 1.3 g of N-(3-chloropropyl)morpholine, and the mixture is stirred at 55° C. for 3 hours. After the completion of the reaction, water is added to the reaction mixture and the mixture is extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure. The obtained oily substance is purified by silica gel column chromatography (chloroform : methanol =10 : 1) and converted into the hydrochloride in methanol, which is recrystallized from methanol to give 0.6 g of 8-(3-morpholinopropoxy)-2-(2-pyridyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one. dihydrochloride.dihydrate as white crystals, m.p. 201°-202° C. (decomposition).

후처리

  1. additionis added to the reaction mixture
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customThe obtained oily substance is purified by silica gel column chromatography (chloroform : methanol =10 : 1)
  7. customis recrystallized from methanol

출처 및 근거

ORD 기록
ord-7cffa23dfa6944f0861fcf7c37eb8a1c
출처 데이터셋
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05045541

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