tert-butyl 7-nitro-3,4-dihydroquinoline-1(2H)-carboxylate → Tert-butyl 7-amino-1,2,3,4-tetrahydroquinoline-1-carboxylate

HRID 1805023ノート

反応式

HRID 1805023 の反応式
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:13][CH:14]=1

参加物

4

反応物 1

HCID 57470252tert-butyl 7-nitro-3,4-dihydroquinoline-1(2H)-carboxylate

生成物 1

HCID 44558562Tert-butyl 7-amino-1,2,3,4-tetrahydroquinoline-1-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A suspension of the crude 7-nitro-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (4.5 g, 16.2 mol) and 10% Pd—C (0.45 g) in MeOH (40 mL) was stirred under H2 (1 atm) at room temperature overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatography (petroleum ether-EtOAc, 5:1) to give tert-butyl 7-amino-3,4-dihydroquinoline-1(2H)-carboxylate (DC-1) as a brown solid (1.2 g, 22% over 2 steps). 1H NMR (CDCl3) δ 7.15 (d, J=2 Hz, 1H), 6.84 (d, J=8 Hz, 1H), 6.36-6.38 (m, 1H), 3.65-3.68 (m, 2H), 3.10 (br s, 2H), 2.66 (t, J=6.4 Hz, 2H), 1.84-1.90 (m, 2H), 1.52 (s, 9H); ESI-MS 496.8 m/z (2M+H+).

後処理

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (petroleum ether-EtOAc, 5:1)

出典と根拠

ORDレコード
ord-f7af3c8591aa45f58a9d6634453851a7
出典データセット
uspto-grants-2013_01
特許番号
US08354427B2

反応ノート

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