Hydrochloric Acid → 7-hydroxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

HRID 542819Notes

Reaction equation

HRID 542819 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[OH-:20].[Na+].Cl>O>[OH:20][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 134744537-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Product 1

HCID 134744287-hydroxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone (5 g) and aqueous sodium hydroxide (5N, 80 ml) was stirred and boiled under reflux for 45 hours. Water (180 ml) was added to the mixture which was then cooled to ambient temperature. The solution was acidified with concentrated hydrochloric acid to pH 4. The resulting precipitate was collected by filtration and washed with boiling industrial methylated spirit (300 ml) and then hot butanol (120 ml). The residue was crystallised from 50% aqueous industrial methylated spirit to give the novel compound 7-hydroxy-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. >320°.

Workup

  1. temperatureunder reflux for 45 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with boiling industrial methylated spirit (300 ml)
  4. customThe residue was crystallised from 50% aqueous industrial methylated spirit

Sources & evidence

ORD record
ord-5d2c9ff77aac41ed877926807d15ffc0
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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