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

HRID 1108629
ノート
印刷プレビュー

反応式

HRID 1108629 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-1953144ce4e74aa9ad268d3db8546ad5
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06069149

反応ノート

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