8-Nitroquinoline → 8-Nitroquinolin-7-amine

HRID 1615633ノート

反応式

HRID 1615633 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I-].C[N+:16](C)(C)N.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[N+:1]([C:4]1[C:5]([NH2:16])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 118308-NitroquinolineHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 129549938-Nitroquinolin-7-amine収率 18%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 8-nitroquinoline (1.88 g, 10 mmol) and 1,1,1-trimethylhydrazinium iodide (3.03 g, 15 mmol) in anhydrous dimethyl sulfoxide (DMSO) (20 mL) was added potassium tert-butoxide (3.36 g, 30 mmol) as a solid. The mixture was stirred at room temperature for 1 h. The mixture was then poured into saturated aqueous ammonium chloride and extracted with EtOAc. The organic layers were concentrated and the residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give 8-nitroquinolin-7-amine as a yellow solid (300 mg, yield 18%). ESI MS: m/z 189 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.93 (dd, 1H, 3.2 Hz, 2J=1.6 Hz), 8.00 (dd, 1H, 1J=6.4 Hz, 2J=1.6 Hz), 7.69 (d, 1H, J=6.8 Hz), 7.29 (dd, 1H, 1J=6.0 Hz, 2J=3.2 Hz), 7.00 (d, 1H, J=7.2 Hz), 5.60 (s, 2H).

後処理

  1. extractionextracted with EtOAc
  2. concentrationThe organic layers were concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with PE/EtOAc v/v 2:1)

出典と根拠

ORDレコード
ord-88d6db43994f4182a9107cdef90ee653
出典データセット
uspto-grants-2014_07
特許番号
US08765760B2

反応ノート

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