Sodium Hydroxide → HCID 20598194, compound

HRID 533664Notes

Reaction equation

HRID 533664 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)OC)=[CH:6][C:5]([C:13]([F:16])([F:15])[F:14])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH3:9][NH:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68091214HCID 68091214, compound

Product 1

HCID 20598194HCID 20598194, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of methyl (2-amino-5-trifluoromethylpyridin-3-yl)-carbamate (100 mg) and THF (15 ml), lithium aluminum hydride (26 mg) was added under ice-cooling. The mixture was stirred for 15 minutes under ice-cooling, heated to 90° C., and stirred with heating for 1.5 hours. Into the reaction mixture cooled to room temperature, aqueous sodium hydroxide solution was poured, and extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 77 mg of N3-methyl-5-trifluoromethylpyridin-2,3-diamine.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. stirringstirred
  5. temperaturewith heating for 1.5 hours
  6. temperatureInto the reaction mixture cooled to room temperature
  7. extractionextracted with tert-butyl methyl ether
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe9ed733182340b19541fecd149d2338
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

Loading…