Hydrochloric Acid → Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1584817Notes

Reaction equation

HRID 1584817 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([Br:26])=[C:8]([F:25])[CH:9]=[C:10]2[C:15]=1[N:14]([CH:16]1[CH2:18][CH2:17]1)[CH:13]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]2=[O:24])(=O)C.C[O-].[Na+].O.Cl>C(O)C>[Br:26][C:7]1[C:6]([CH2:5][OH:4])=[C:15]2[C:10]([C:11](=[O:24])[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][N:14]2[CH:16]2[CH2:18][CH2:17]2)=[CH:9][C:8]=1[F:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 21220351HCID 21220351, compound

Product 1

HCID 21220404Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 58 ml of ethanol was suspended 1.46 g of ethyl 8-acetoxymethyl-7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, and 19 mg of sodium methoxide was added to the suspension, after which the resulting mixture was stirred at room temperature for seven hours. To the reaction mixture was added 60 ml of water and the pH was adjusted to 7 with 1N hydrochloric acid, after which the crystals formed were collected by filtration, to obtain 1.28 g of colorless, crystalline ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. additionwas added to the suspension
  2. customafter which the crystals formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8fbafc71836c47dba1b113b8cfc4330b
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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