Hydrogen Bromide → Ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3quinolinecarboxylate

HRID 868092Notes

Reaction equation

HRID 868092 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:21])[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][C:5]=1[F:22])(=[O:3])[CH3:2].[Br:23]([O-])(=O)=O.[K+].Br>C(O)(=O)C>[Br:23][CH2:2][C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:21])[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][C:5]=1[F:22])=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 13772817Ethyl 7-acetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateHCID 23673461Potassium Bromate

Product 1

HCID 13853634Ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3quinolinecarboxylateYield 271.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.45 g (8.0 mmol) ethyl 7-acetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 50 ml acetic acid was treated with 0.46 g potassium bromate, and then 3.8 ml 48% hydrobromic acid was added dropwise over one half hour. The mixture was stirred 24 hours at room temperature and poured into 200 ml ice water. The precipitate was filtered, washed with water and dried to afford 2.87 g ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-124782b203944a5bac331b7cc17407c7
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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