Hydrazine → 3-Amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one

HRID 1169694Notes

Reaction equation

HRID 1169694 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:5]=1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[C:9]([N+:26]2C=CC=CC=2)[C:8]1=[O:32].NN>C(O)C>[NH2:26][C:9]1[C:8](=[O:32])[N:7]([CH2:6][C:5]2[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:4]=2[O:3][CH3:2])[C:16]2[C:11]([C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866117061-[1-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride

Product 1

HCID 588522503-Amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride (225 mg, 0.422 mmol) and hydrazine (0.133 mL, 4.22 mmol) in 3 mL of ethanol was heated to reflux. After one hour, the reaction was cooled to room temperature. The reaction was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography through SiO2 (0-5% MeOH/CH2Cl2) to provide the titled product as a white foam. 1H-NMR (500 MHz, CDCl3) δ 7.55 (m, 1H), 7.18 (d, J=8.5 Hz, 2H), 7.12 (m, 1H), 6.81 (dd, J=9.2, 2.7 Hz, 1H), 6.76 (d, J=8.5 Hz, 1H), 6.52 (br s, 1H), 6.34 (dd, J=8.5, 2.2 Hz, 1H), 5.57 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 3.65 (s, 3H) ppm. HRMS (ES) exact mass calculated for C25H23FN2O4 (M+H+): 435.1715. Found 435.1732.

Workup

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography through SiO2 (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-59ae8db5a5d743238efadb32a6f57287
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

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