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

HRID 1108624

反応式

HRID 1108624 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-84d058dba5b743769543c5eb60a6f701
出典データセット
uspto-grants-2000_05
特許番号
US06069149

関連ノート

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