Aniline → HCID 68575021、化合物

HRID 40805

反応式

HRID 40805 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.NC1C=CC=CC=1.[Br:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:11]=[C:10]([O:12][CH2:23][CH2:22][CH2:21][Br:20])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 1784288112-Methylquinolin-4-ol

生成物 1

HCID 68575021HCID 68575021、化合物収率 64%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 2-methylquinolin-4-ol (1.59 g, 10 mmol) (synthesized from aniline and acetoacetic ester according to a procedure known in the art: see Leonard et al. (1946) J. Am. Chem. Soc. 68:1279-1281), 1,3-dibromopropane (8.08 g, 40 mmol) and potassium carbonate (1.659 g, 12 mmol) in acetone (50 mL) was refluxed until the starting material disappeared. The reaction mixture was filtered and after evaporation of solvent residue was purified by column chromatography on silica gel (1% MeOH: 99% CH2Cl2 as eluent). The product was obtained as light yellow solid (1.793 g, 64%). 1H NMR (400 MHz, CDCl3): 2.48 (2H, m), 2.69 (3H, s), 3.69 (2H, t, J=6.3 Hz), 4.33 (2H, t, J=5.8 Hz), 6.6 (1H, s), 7.43 (1H, t, J=7.5 Hz), 7.66 (1H, t, J=7.8 Hz), 7.95 (1H, d, J=8.5 Hz), 8.12 (1H, d, J=8.3 Hz).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customafter evaporation of solvent residue
  3. customwas purified by column chromatography on silica gel (1% MeOH: 99% CH2Cl2 as eluent)

出典と根拠

ORDレコード
ord-afe4411a86864a6da4827fedd6050ce9
出典データセット
uspto-grants-2013_09
特許番号
US08530491B2

関連ノート

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