Chloroform → HCID 15017604, compound

HRID 1460953Notes

Reaction equation

HRID 1460953 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:7]=3[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl.C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl>CN(C)C=O.O>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:7]=3[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 11989638HCID 11989638, compound

Product 1

HCID 15017604HCID 15017604, compoundYield 133.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In dry N,N-dimethylformamide was dissolved 6.0 g of 3-hydroxy-5H-benzofuro[3,2-c]quinolin-6-one, and 1.1 g of 2-dimethylaminoethyl chloride hydrochloride and 6.02 g of sodium bicarbonate were added to the solution. The mixture was stirred for 16 hours at 120° C. Into the reaction mixture were poured chloroform and water, and the insolved materials were filtered out. The organic layer was washed with water, dried over magnesium sulfate anhydride, and evaporated under reduced pressure. The residue was washed with ether, and recrystallized from chloroform and ethyl acetate to obtain 3.29 g of 3-(2-dimethylaminoethoxy)-5H-benzofuro[3,2-c]quinolin-6-one.

Workup

  1. additionwere added to the solution
  2. filtrationthe insolved materials were filtered out
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated under reduced pressure
  6. washThe residue was washed with ether
  7. customrecrystallized from chloroform and ethyl acetate

Sources & evidence

ORD record
ord-e966d052adbd422389dd320f3db8400f
Source dataset
uspto-grants-1991_12
Patent number
US05073553

Reaction notes

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