Potassium Carbonate → HCID 71255482, compound

HRID 540336

Reaction equation

HRID 540336 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7](Cl)[CH:6]=1)=[O:4].Cl.[CH2:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20][CH2:19][NH:18]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20][CH2:19][N:18]1[C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5202936Methyl 2-chloroquinoline-4-carboxylateHCID 178487942,3,4,5-Tetrahydro-1H-2-benzazepine--hydrogen chloride (1/1)

Product 1

HCID 71255482HCID 71255482, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 2-chloroquinoline-4-carboxylic acid methyl ester (3 g, 13.5 mmol), 2,3,4,5-tetrahydro-1H-2-benzazepine hydrochloride (3 g, 16.3 mmol), potassium carbonate (4.5 g, 32.6 mmol), tetrabutylammonium iodide (300 mg) and toluene (60 mL) was heated with stirring at 110° C. for 5 days. The solvent was removed under reduced pressure to give a residue which was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4) to give 1.97 g of product as a yellow solid. MS obsd. (ESI+) [(M+H)+] 333.

Workup

  1. temperaturewas heated
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue which
  4. customwas purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4)

Sources & evidence

ORD record
ord-19110ca4eced459bbf086d9bfde407b0
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Linked notes

Loading…