Aluminium lithium hydride → HCID 83877737, compound

HRID 1754385Notes

Reaction equation

HRID 1754385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([NH:13][CH:14]=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.[OH-].[NH4+].CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([NH:13][CH3:14])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86724386HCID 86724386, compound

Product 1

HCID 83877737HCID 83877737, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of N-[1-(4-fluorophenyl)pyrazol-4-yl]formamide (0.275 g, 1.33 mmol) and LiAlH4 (1.33 mL, 2.66 mmol, 2 M in THF) in THF (5 mL) was heated at 45° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with 5 mL of concentrated ammonium hydroxide and 80 mL of 20% MeOH/CH2Cl2. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-100% EtOAc/CH2Cl2 gradient elution) to give 1-(4-fluorophenyl)-N-methylpyrazol-4-amine as an oil (0.23 g, 90%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2, 0-100% EtOAc/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-e789903b0fd94a669f5c496f8c8b4779
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

Loading…