Aniline → HCID 68575021, compound

HRID 40805

Reaction equation

HRID 40805 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 68575021HCID 68575021, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-afe4411a86864a6da4827fedd6050ce9
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Linked notes

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