Acetic Anhydride → 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

HRID 542827Notes

Reaction equation

HRID 542827 reaction equation
[C:1](OC(=O)C)(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[CH2:16][C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)=[C:11]([NH:24][CH3:25])[CH:10]=1>C(O)=O>[F:8][C:9]1[CH:10]=[C:11]2[C:12]([C:15](=[O:23])[C:16]([C:17]3[N:21]([CH3:22])[N:20]=[N:19][N:18]=3)=[CH:25][N:24]2[CH3:1])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 134743941-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

Product 1

HCID 134744537-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of acetic anhydride (0.8 ml) and formic acid (0.4 ml) was stirred at 50°-60° for 2 hours, then cooled to ambient temperature. 1-(4-Fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone (1.03 g) was added. The mixture was stirred at ambient temperature for 5 hours, then kept at this temperature for 16 hours. The mixture was triturated under light petroleum to give a solid product. This product was extracted with boiling ethyl acetate (100 ml) and the extract cooled to give a solid product which was recrystallised from industrial methylated spirit to give the novel compound 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. 264°-267°, identical to the product of Example 2(d).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 5 hours
  2. waitkept at this temperature for 16 hours
  3. customThe mixture was triturated under light petroleum
  4. customto give a solid product
  5. extractionThis product was extracted with boiling ethyl acetate (100 ml)
  6. temperaturethe extract cooled
  7. customto give a solid product which
  8. customwas recrystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-2643c1bc739042ee89fffc15a694f755
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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