Water → 4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-6-nitro-2(1H)-quinolinone

HRID 2209974Notes

Reaction equation

HRID 2209974 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[NH:7][C:6](=[O:17])[CH:5]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)[CH2:20][CH2:19]1.C(=O)([O-])O.[Na+].O>CN(C)C=O>[NH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:2][CH2:3][C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=4)[NH:7][C:6](=[O:17])[CH:5]=3)[CH2:19][CH2:20]2)=[CH:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 193797214-(2-bromoethyl)-6-nitro-2(1H)-quinolinone

Product 1

HCID 193796784-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-6-nitro-2(1H)-quinolinoneYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-(2-bromoethyl)-6-nitro-2(1H)-quinolinone (II-9) (891 mg, 3.0 mmol), 3-(4-piperidinyl)-1H-indol (600 mg, 3.0 mmol) and sodium hydrogen carbonate (378 mg, 4.5 mmol) in dimethylformamide (9 ml) was stirred at 50 ° C. for 30 hours. Then the reaction mixture was poured into water. The precipitated solid was filtered, washed with water, dried and recrystallized from a mixed solvent consisting of methanol, tetrahydrofuran and water to give the desired compound (III-19) (640 mg, yield 51.2%) as pale yellow crystals, mp 251°-253 ° C. (recrystallized from a mixture of methanol, tetrahydrofuran and water).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried
  4. customrecrystallized from a mixed solvent

Sources & evidence

ORD record
ord-9d1a3944718e4623829f4d5cf3eeba72
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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