Acetic Acid → HCID 21280189, compound

HRID 637762Notes

Reaction equation

HRID 637762 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 220 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 220 g of silica gel
  5. washeluting with 97.5:2.5 (v/v) CH2Cl2
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5014af34547849518780b49e388de8f9
Source dataset
uspto-grants-1985_12
Patent number
US04558130

Reaction notes

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