Acetic Acid → HCID 21280189, compound

HRID 414702Notes

Reaction equation

HRID 414702 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[Mg].C(O)(=O)C>CO>[CH3:1][N:2]([CH3:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 339524HCID 339524, compoundHCID 5462224Magnesium

Product 1

HCID 21280189HCID 21280189, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g (5.7 mmol) of 7-dimethylamino-2-quinolone [A. Rice, Ann. Chim. 48: 958-996(1958)] in 40 mL of MeOH was added 1.3 g (5.7 mmol) of magnesium. The reaction was warmed gently on a steam bath, and then was allowed to stir for two hours at room temperature. Acetic acid (8 mL) was then added and the solution filtered. The filtrate was concentrated and the residue chromatographed on 200 g of silica gel, eluting with 97.5:2.5 (v/v) CH2Cl2 :MeOH. Fractions 50-60 (12 mL/fraction) were combined and concentrated to yield 0.4 g of the dihydroquinolone as a white solid, m.p. 154°-156° C.

Workup

  1. temperatureThe reaction was warmed gently on a steam bath
  2. filtrationthe solution filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue chromatographed on 200 g of silica gel
  5. washeluting with 97.5:2.5 (v/v) CH2Cl2
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bf5a82612164f66acb835b81333d67b
Source dataset
uspto-grants-1988_12
Patent number
US04794079

Reaction notes

Loading…