Water → N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine

HRID 542852

반응식

HRID 542852 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][CH:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:21].S(Cl)([Cl:24])=O.O.[OH-].[NH4+]>ClCCl>[Cl:24][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 86741428HCID 86741428, 화합물

생성물 1

HCID 608631N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 7.8 g (0.027 mole) of 6-[(6-methoxy-4-methyl-8-quinolinyl)amino-1-hexanol in 90 ml of dichloromethane at 5° was added dropwise a solution of 1.9 ml (0.03 mole) of thionylchloride in 25 ml of dichloromethane. The mixture was allowed to warm to room temperature overnight, poured into iced water, and made basic with concentrated ammonium hydroxide. The resulting emulsion was filtered and the layers then separated. The organic portion was washed, dried, and concentrated to afford 7.9 g (96%) of crude product which was used in the next step without further purification. TLC(silica--thyl acetate) indicated that the product, Rf=0.65, was slightly contaminated with the starting hexanol, Rf=0.4.

후처리

  1. filtrationThe resulting emulsion was filtered
  2. customthe layers then separated
  3. washThe organic portion was washed
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e7c025f4b11c41b3b07cdfe3e7f0cba7
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659708

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