Sodium Hydroxide → HCID 13338836, compound

HRID 1285495Notes

Reaction equation

HRID 1285495 reaction equation
[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[C:14]2S)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[OH-].[Na+]>[N+]([O-])(O)=O>[F:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178422903HCID 178422903, compound

Product 1

HCID 13338836HCID 13338836, compound

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a flask containing 16.2 g (0.0625 mole) of 6-fluoro-5-(2-mercaptoimidazol-1-yl)-2-methylquinoline was added with stirring 300 ml of 20% nitric acid. After stirring for 30 minutes, the mixture was heated on a steam bath for an additional 30 minutes. The solution was allowed to cool to about 20° C., then made basic (pH 8 to 10) by adding 50% aqueous sodium hydroxide while cooling with an ice bath. The solid precipitate was separated by filtration, washed with water and dried. Recrystallization from aqueous ethanol provided 6-fluoro-5-(imidazol-1-yl)-2-methylquinoline, m.p. 159°-161° C. Analysis: Calculated for C13H10FN3 : %C, 68.7; %H, 4.4; %N, 18.5; Found: %C, 68.6; %H, 4.4; %N, 18.2.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated on a steam bath for an additional 30 minutes
  3. temperaturewhile cooling with an ice bath
  4. customThe solid precipitate was separated by filtration
  5. washwashed with water
  6. customdried
  7. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-72c0810452ee47cabd6624bdc3e3a35c
Source dataset
uspto-grants-1986_01
Patent number
US04567269

Reaction notes

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