Potassium Nitrate → 5-Bromo-6-fluoro-8-nitroquinaldine

HRID 1583598Notes

Reaction equation

HRID 1583598 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([CH3:18])=[N:12]2>S(=O)(=O)(O)O.ClCCl>[Br:6][C:7]1[C:16]([F:17])=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([CH3:18])=[N:12]2

Participants

5

Reactant 2

HCID 24434Potassium NitrateHCID 130353135-Bromo-6-fluoro-2-methylquinoline

Product 1

HCID 131919625-Bromo-6-fluoro-8-nitroquinaldineYield 91.8%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.5 g of potassium nitrate in 30 ml of concentrated sulfuric acid was added to 21.0 g of 5-bromo-6-fluoroquinaldine in 117 ml of concentrated sulfuric acid dropwise at -5° C. After stirring at room temperature for 5 hours, the reaction mixture was poured into 2 l of ice water to precipitate solids which were then collected by filtration. The filtrate was rendered alkaline to form a small amount of solids, which together with the former solids were dissolved in dichloromethane. After the solution was dried over sodium sulfate the solvent was distilled off. Recrystallization of the residue from isopaopanol gave 22.9 g of 5-bromo-6-fluoro-8-nitroquinaldine. m.p. 135°-137° C.

Workup

  1. customto precipitate solids which
  2. filtrationwere then collected by filtration
  3. customto form a small amount of solids, which together with the former solids
  4. dry with materialAfter the solution was dried over sodium sulfate the solvent
  5. distillationwas distilled off
  6. customRecrystallization of the residue from isopaopanol

Sources & evidence

ORD record
ord-3b348d87d0964ae488d9e0f91816ae67
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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