Sodium Carbonate → HCID 10615023, compound

HRID 1647721Notes

Reaction equation

HRID 1647721 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[N:15]12[CH2:22][CH2:21][CH2:20][C:19]1([CH2:23][NH2:24])[CH2:18][CH2:17][CH2:16]2.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[N:15]12[CH2:22][CH2:21][CH2:20][C:19]1([CH2:23][NH:24][C:2]1[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH2:18][CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10654304(Hexahydro-1H-pyrrolizin-7A-YL)methanamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 10615023HCID 10615023, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
17.5 °C

Procedure

In 60.0 ml of dimethylformamide (DMF) was dissolved 7.90 g (36.8 mmol) of 4-chloro-3-nitroquinoline, and 5.66 g (40.5 mmol) of (1-azabicyclo[3.3.0]octan-5-yl)methylamine was added to the solution under cooling with ice. After stirring at 15 to 20° C. for 20 hours, the reaction mixture was poured into 400 ml of ice-water and rendered basic with sodium carbonate. The thus formed precipitate was collected by filtration, washed with water, and dried in a desiccator under reduced pressure to obtain 10.6 g (yield: 92.2%) of the titled compound as a yellow powder.

Workup

  1. additionwas added to the solution
  2. temperatureunder cooling with ice
  3. filtrationThe thus formed precipitate was collected by filtration
  4. washwashed with water
  5. customdried in a desiccator under reduced pressure

Sources & evidence

ORD record
ord-8a0916a63a0f456b96ccc1b6db13fe99
Source dataset
uspto-grants-1995_07
Patent number
US05434165

Reaction notes

Loading…