Hydrochloric Acid → 5,6,7,8-Tetrahydro-3-methyl-8-(4-nitrobenzamido) quinoline

HRID 359461노트

반응식

HRID 359461 반응식
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].CCOCC.Cl.Cl>C(Cl)Cl.C(N(CC)CC)C>[CH3:12][C:8]1[CH:9]=[N:10][C:11]2[CH:2]([NH:1][C:20](=[O:21])[C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=3)[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 10953452Ether hydrochlorideHCID 123582203-Methyl-5,6,7,8-tetrahydroquinolin-8-amine

생성물 1

HCID 146209795,6,7,8-Tetrahydro-3-methyl-8-(4-nitrobenzamido) quinoline

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To 8-amino-5,6,7,8-tetrahydro-3-methylquinoline (4.5g, 2.27 M moles) in CH2Cl2 was added 4-nitrobenzoylchloride (4.2g, 2.26Mmoles) followed by sufficient triethylamine to clear the solution and then form a new precipitate. This material was left overnight and then the solvent removed. The residue was taken up in 2M HCl and washed with ethyl acetate. The aquous layer was then basified with Na2CO3 and extracted with chloroform. The organic solution was dried (MgSO4) and evaporated under reduced pressure to give a residue which was treated with Et2O/HCl to give a white solid identified by infra-red and nmr specroscopy as the hydrochloride of the title compound.

후처리

  1. customform a new precipitate
  2. customthe solvent removed
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give a residue which
  8. customto give a white solid

출처 및 근거

ORD 기록
ord-85bf64d36df24e19b086bfe8a5bafa85
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001131

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