Water → 4-((2-Nitro-4-(quinolin-2-ylmethoxy)phenylamino)methyl)benzonitrile

HRID 2178433Notes

Reaction equation

HRID 2178433 reaction equation
F[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[NH2:23][CH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.O>C(#N)C>[N+:20]([C:3]1[CH:4]=[C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:18]=[CH:19][C:2]=1[NH:30][CH2:29][C:28]1[CH:31]=[CH:32][C:25]([C:24]#[N:23])=[CH:26][CH:27]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 826084-(Aminomethyl)benzonitrileHCID 904169762-((4-Fluoro-3-nitrophenoxy)methyl)quinoline

Product 1

HCID 904141084-((2-Nitro-4-(quinolin-2-ylmethoxy)phenylamino)methyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-((4-fluoro-3-nitrophenoxy)methyl)quinoline (298 mg, 1 mmol) and 4-(aminomethyl)benzonitrile (132 mg, 1 mmol) in acetonitrile (1 mL) was added DIPEA (2 mL, 12 mmol). The mixture was stirred at 80° C. overnight. The mixture was cooled to RT, water (20 mL) was added, and the mixture was extracted with DCM (3×20 mL). The organics were combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to dryness. The residue was recrystallized from ethanol to give 4-((2-nitro-4-(quinolin-2-ylmethoxy)phenylamino)methyl)benzonitrile. The recrystallized 4-((2-nitro-4-(quinolin-2-ylmethoxy)phenylamino)methyl)benzonitrile (307 mg, 0.75 mmol) was then dissolved in ethanol (20 mL) and SnCl2.2H2O (1 g, 4.5 mmol) was added. The resulting mixture was stirred at 90° C. overnight. The mixture was cooled to RT and the pH adjusted to ˜pH 8-9 by the addition of sat. aq. NaHCO3. The aqueous mixture was stirred at RT for 30 min. and then extracted with DCM (3×20 mL). The organics were combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to dryness to afford the title compound, which was used without further purification. MS (ESI): mass calcd. for C24H20N4O, 380.16; m/z found, 381.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionthe mixture was extracted with DCM (3×20 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3efbe73c135142d28010281abc1b5a45
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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