Benzyl (3-aminopropyl)carbamate → 4-[3-(Benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

HRID 1108624

반응식

HRID 1108624 반응식
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][NH2:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][NH:30][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 417669Benzyl (3-aminopropyl)carbamateHCID 27851382,4-Dichloro-3-nitroquinoline

생성물 1

HCID 187839664-[3-(Benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline수율 84.8%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

0.19 g (0.768 mmol) of 2,4-dichloro-3-nitroquinoline and 0.16 g (0.768 mmol) of N-(benzyloxycarbonyl)-1,3-propanediamine was heated at 70° C. in 5 ml of triethylamine for one hour with stirring. After triethylamine was distilled off under reduced pressure, the residue was dissolved in methylene chloride, washed with water, and dried (MgSO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v)) to obtain 0.27 g (0.651 mmol) of 4-[3-(benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline shown below as yellow powder. ##STR29## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) :1.79 (2H, m), 3.35 (4H, m), 5.02 (1H, br), 5.18 (2H, s), 7.15 (1H, br), 7.37 (5H, m), 7.57 (1H, t, J=8.0 Hz), 7.73 (1H, t, J=7.8 Hz), 7.90 (1H, d, J=8.4 Hz), 8.21 (1H, d, J=8.0 Hz).

후처리

  1. distillationAfter triethylamine was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v))

출처 및 근거

ORD 기록
ord-84d058dba5b743769543c5eb60a6f701
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069149

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