4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione → HCID 86624647, compound

HRID 2196525Notes

Reaction equation

HRID 2196525 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.[F:10][C:11]([F:23])([F:22])[C:12](=O)[CH2:13][C:14]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)=O>CC(O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[CH:13][C:12]([C:11]([F:23])([F:10])[F:22])=[N:9]2)[N:3]=1

Participants

5

Reactant 2

HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 3200042-Chloro-6-hydrazinopyridine

Product 1

HCID 86624647HCID 86624647, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 2-chloro-6-hydrazinopyridine (300 mg, 2.09 mmol) in 2-propanol (10.4 mL), was added 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (0.310 mL, 2.090 mmol) followed by 2 drops of conc HCl. The resulting mixture was heated to reflux overnight and then evaporated to dryness. A 2:1 mixture of regioisomeric products 45 (588 mg, 90% yield) were isolated as a pale yellow oil. LRMS (ESI): calc. 313.6; found 313.6 (M)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-753905b235234106bd399688c43a4a71
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

Loading…