Aniline → HCID 68575021, 화합물

HRID 40805

반응식

HRID 40805 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 68575021HCID 68575021, 화합물수율 64%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-afe4411a86864a6da4827fedd6050ce9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530491B2

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