Potassium Carbonate → HCID 24771033, compound

HRID 1670708Notes

Reaction equation

HRID 1670708 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:16]=[CH:17][C:18]2[N:40]([CH:41]=1)[C:21]1[N:22]([C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)[C:23](=[O:30])[C:24]3[C:29]([C:20]=1[N:19]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3>CN(C=O)C>[N+:37]([C:34]1[CH:33]=[CH:32][C:31]([N:22]2[C:21]3[N:40]4[CH:41]=[C:15]([O:14][CH2:6][C:5]([O:4][CH2:3][CH3:2])=[O:7])[CH:16]=[CH:17][C:18]4=[N:19][C:20]=3[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:30])=[CH:36][CH:35]=1)([O-:39])=[O:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 24771030HCID 24771030, compound

Product 1

HCID 24771033HCID 24771033, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoethylacetate (1.2 equiv., 1.128 mmol, 0.188 g) and potassium carbonate (3.0 equiv., 2.820 mmol, 0.390 g) were added to a solution of 10 (1.0 equiv., 0.940 mmol, 0.350 g) in DMF (10 ml). The mixture was heated at reflux for 2 h. The reaction product was precipitated by the addition of water, filtered off and washed with isopropanol and isopropyl ether successively to give ethyl 2-[[5,6-dihydro-6-(4-nitrophenyl)-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl]oxy]-acetate (13) (0.409 g, yield=95%, purity (LC)=92%) as a light red powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe reaction product was precipitated by the addition of water
  4. filtrationfiltered off
  5. washwashed with isopropanol and isopropyl ether successively

Sources & evidence

ORD record
ord-d264ad69715b4e16baaa657a054cf76d
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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