Sodium Methoxide → HCID 11740606, compound

HRID 1681205Notes

Reaction equation

HRID 1681205 reaction equation
C([C:3]1[N:4]([CH:27]2[CH2:29][CH2:28]2)[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[CH:9][C:8]([F:17])=[C:7]([C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([CH2:25]Cl)[CH:19]=1)[CH:6]=2)C.[CH3:30][O-:31].[Na+]>CO>[CH:27]1([N:4]2[C:5]3[C:10](=[CH:9][C:8]([F:17])=[C:7]([C:18]4[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([CH2:25][O:31][CH3:30])[CH:19]=4)[CH:6]=3)[C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:3]2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19807255HCID 19807255, compound

Product 1

HCID 11740606HCID 11740606, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.52 g ethyl 1-cyclopropyl-7-[2-(chloromethyl)-6-methyl-4-pyridinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Example 18b) in 125 ml methanol was treated with 1.5 g of powdered sodium methoxide, and the reaction mixture was heated at reflux for about 16 hours. The mixture was quenched in ice containing acetic acid and extracted with methylene dichloride. The extracts were concentrated and the residue treated with water. The solid product was collected and dried (1.11 g) and was recrystallized from ethyl acetate/hexane to give 0.91 g 1-cyclopropyl-6-fluoro-7-[2-(methoxymethyl)-6-methyl-4-pyridinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, m.p. 192°-193° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for about 16 hours
  3. customThe mixture was quenched in ice
  4. additioncontaining acetic acid
  5. extractionextracted with methylene dichloride
  6. concentrationThe extracts were concentrated
  7. additionthe residue treated with water
  8. customThe solid product was collected
  9. customdried (1.11 g)
  10. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4a94d26225b477997a3168e23bb4229
Source dataset
uspto-grants-1992_12
Patent number
US05169853

Reaction notes

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