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Hydrochloric Acid → 3-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline

HRID 1108625
ノート
印刷プレビュー

反応式

HRID 1108625 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([Cl:26])[C:17]=1[N+:27]([O-])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO.[Fe]>[NH2:27][C:17]1[C:18]([Cl:26])=[N:19][C:20]2[C:25]([C:16]=1[NH:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[CH:24][CH:23]=[CH:22][CH:21]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 187839664-[3-(Benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

生成物 1

HCID 187839713-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline収率 47.9%

試薬・触媒・溶媒 2

HCID 23925Iron触媒
HCID 887
Methanol
溶媒

実験手順

0.27 g (0.651 mmol) of 4-[3-(benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 10 ml of methanol. One ml of concentrated hydrochloric acid and 0.22 g (0.390 mmol) of iron powder were added thereto and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a saturated sodium hydrogencarbonate aqueous solution. After the resulting mixed solution was extracted with ethyl acetate, the extract was washed with brine and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v)) to obtain 0.12 g (0.312 mmol) of 3-amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline shown below as faint yellow powder. ##STR30## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) :1.76 (2H, m), 3.30 (2H, m), 3.42 (2H, q, J=6.3 Hz), 4.21 (2H, b r), 4.44 (1H, br), 4.92 (1H, br), 5.16 (2H, s), 7.30~7.39 (5H, m), 7.46 (2H, m), 7.89 (2H, m).

後処理

  1. additionAfter the resulting mixed solution
  2. extractionwas extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v))

出典と根拠

ORDレコード
ord-bc3dcd04d8c8482a85b7e7727cbd4f03
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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