Potassium Hydroxide → HCID 18918333, compound

HRID 1290484Notes

Reaction equation

HRID 1290484 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, compound

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 (M+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-53a8ac01a2b74c95bfca2b354a8d7e11
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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