Hydrochloric Acid → 1-Hydroxyfluromidine

HRID 1658356Notes

Reaction equation

HRID 1658356 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=O)[C:5]([NH:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=1.Cl.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[N:15]([OH:17])[C:9]([C:10]([F:13])([F:12])[F:11])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 20355442N-(5-Chloro-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 30824181-Hydroxyfluromidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Chloro-3-nitro-2-(trifluoroacetamido)pyridine (2.7 grams), anhydrous stannous chloride (3.8 grams), and 4.0 milliliters of concentrated hydrochloric acid were mixed in 20 milliliters of acetic acid. The mixture was cooled to temperatures of 0°-10°C. and maintained thereat for 15 minutes. Water (50 milliliters) was then added to the reaction mixture, and the desired 6-chloro-1-hydroxy-2-(trifluoromethyl)imidazo(4,5-b)-pyridine product precipitated. It was separared and dried. The yield was 1.3 grams, 55 percent. The product so obtained melted at 264°-66°C.

Workup

  1. temperatureThe mixture was cooled to temperatures of 0°-10°C.
  2. temperaturemaintained
  3. customthe desired 6-chloro-1-hydroxy-2-(trifluoromethyl)imidazo(4,5-b)-pyridine product precipitated
  4. customdried

Sources & evidence

ORD record
ord-12f37d6948344609a09469eb2b9be718
Source dataset
uspto-grants-1976_06
Patent number
US03963734

Reaction notes

Loading…