Potassium Hydroxide → HCID 18918333, compound

HRID 1291827Notes

Reaction equation

HRID 1291827 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:26][CH2:25][N:24](C(OCC)=O)[CH2:23][CH2:22]2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18918290HCID 18918290, compound

Product 1

HCID 18918333HCID 18918333, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of step (iv) (1.8 g), ethanol (40 ml) and 20% w/v aqueous potassium hydroxide solution (40 ml) was heated to reflux overnight, cooled and evaporated to dryness. The residue was partitioned between water and dichloromethane and the organic layer was separated, washed with brine, dried (MgSO4) and evaporated to yield 1-benzyl-3-(piperazin-1-yl)-7-methoxy-4-quinolone (1.5 g) as a yellow foam: NMR (CDCl3) δ 2.80 (1H, m), 3.20 (8H, m), 3.73 (3H, s), 5.28 (2H, s), 6.59 (1H, d), 6.88 (1H, dd), 7.15 (3H, m), 7.30 (3H, m), 8.41 (1H, d); m/Z 350 (N+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was partitioned between water and dichloromethane
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-60aa50df186e4553bc69867c4c22bb8c
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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