Potassium Nitrate → HCID 13191963, compound

HRID 434668Notes

Reaction equation

HRID 434668 reaction equation
[Br:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:11]([Cl:12])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 2749765-bromo-6-chloro-2-methylquinoline

Product 1

HCID 13191963HCID 13191963, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Bromo-6-chloroquinaldine (40 g) was dissolved in 220 ml of concentrated sulfuric acid. After cooling to 0° C., a solution of 20.5 g of potassium nitrate in 60 ml of concentrated sulfuric acid was added dropwise to the resulting solution in 30 minutes followed by stirring at room temperature for 2.5 hours. The reaction mixture was poured into 1.5 l of ice water and crystals which formed were collected by filtration. The filtrate was rendered alkaline to give a small amount of solids which together with the former solids were recrystallized from isopropanol to give 42.3 g of 5-bromo-6-chloro-8-nitroquinaldine. m.p. 141°-142° C.

Workup

  1. customformed
  2. filtrationwere collected by filtration
  3. customto give a small amount of solids which together with the former solids
  4. customwere recrystallized from isopropanol

Sources & evidence

ORD record
ord-3e1762d5d79a4d199003813ba77e4428
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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