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Ammonia → 3-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline

HRID 1108629
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HRID 1108629 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([Cl:23])[C:14]=1[N+:24]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.N>C(O)C>[NH2:24][C:14]1[C:15]([Cl:23])=[N:16][C:17]2[C:22]([C:13]=1[NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:21][CH:20]=[CH:19][CH:18]=2
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참가 물질

5

반응물 3

HCID 222AmmoniaHCID 24287Tin tetrachlorideHCID 187839794-[3-(Tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

생성물 1

HCID 187839403-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline수율 61.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

0.27 g (0.70 mmol) of 4-[3-(tert-Butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 7 ml of ethanol. Tin chloride [II] dihydrate (0.55 g, 2.45 mmol) was added thereto and the mixture was refluxed under heating for 1 hour. After cooling, the reaction mixture was poured into 2N aqueous ammonia. The resulting solution was extracted twice with chloroform, thereafter the extract was washed (brine), and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v)) to obtain 0.15 g (0.428 mmol) of 3-amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline shown below as pale yellow crystals. ##STR35## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) : 1.49 (9H, s), 1.73 (2H, m), 3.29 (2H, t, J=6.2 Hz), 3.35 (2H, q, J=6.0 Hz), 4.28 (2H, br), 4.60 (1H, br), 4.75 (1H, br), 7.44 (2H, m), 7.87 (1H, d, J=7.6 Hz), 7.94 (1H, d, J=7.6 Hz).

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. temperatureAfter cooling
  4. extractionThe resulting solution was extracted twice with chloroform
  5. washthe extract was washed (brine)
  6. dry with materialdried (Na2SO4)
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v))

출처 및 근거

ORD 기록
ord-1953144ce4e74aa9ad268d3db8546ad5
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06069149

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