Sulfuric Acid → 2-[(4-(2-Methyl-4-(pyridin-4-yl)-2H-pyrazol-3-yl)phenoxy)methyl]quinoline

HRID 33823

Reaction equation

HRID 33823 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[N:10][NH:9][C:8]=2[C:12]2[CH:29]=[CH:28][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.[CH3:30]NN.S(=O)(=O)(O)O>C(O)C>[CH3:30][N:9]1[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:28][CH:29]=2)=[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6061MethylhydrazineHCID 116105532-((4-(4-pyridin-4-yl-1H-pyrazol-3-yl)phenoxy)methyl)quinoline

Product 1

HCID 116683042-[(4-(2-Methyl-4-(pyridin-4-yl)-2H-pyrazol-3-yl)phenoxy)methyl]quinolineYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl}-quinoline (1.72 g) in ethanol (20 ml) was added methyl hydrazine (3.5 ml, 1.5 eq.) and concentrated sulfuric acid (0.1 ml). The reaction mixture was stirred 1 h at ambient temperature and solvent evaporated. The reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Preparative HPLC chromatography provided the title compound (minor isomer) as a white solid (0.30 g, 17%). 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=5.4 Hz, 2 H), 8.21 (d, J=8.7 Hz, 1 H), 7.80 (d, J=8.3 Hz, 1H), 7.77 (s, 1 H), 7.66 (m, 3 H), 7.53 (m, 1H), 7.19 (d, J=8.7 Hz, 2 H), 7.11 (d, J=8.7 Hz, 2H), 7.01 (d, J=6.2 Hz, 2H) 5.40 (s, 2H), 3.69 (s, 3H); MS: (M+H m/z=393.3).

Workup

  1. customsolvent evaporated
  2. customThe reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate
  3. customThe layers were separated
  4. filtrationthe organic layer dried magnesium sulfate, filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2b7e7648a04fd6b6ad30b2435afe5d
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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