Ammonium Chloride → HCID 67396693, compound

HRID 70506Notes

Reaction equation

HRID 70506 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C:10]2[CH:11]=[CH:12][C:13]([C:18](OCC)=[O:19])=[N:14][C:15]=2[O:16][CH3:17])[CH2:9][CH2:8]1.[Cl-].[NH4+]>O1CCCC1>[CH:7]1([C:10]2[CH:11]=[CH:12][C:13]([CH2:18][OH:19])=[N:14][C:15]=2[O:16][CH3:17])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 67396424HCID 67396424, compound

Product 1

HCID 67396693HCID 67396693, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (4.44 g) was added in small portions to a solution of ethyl 5-cyclopropyl-6-methoxypyridine-2-carboxylate (17.3 g) in tetrahydrofuran (300 mL) under ice-cooling, and the mixture was stirred at the same temperature for one hour. The reaction solution was poured into a saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure to give (5-cyclopropyl-6-methoxypyridin-2-yl)methanol (14.1 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationafter which the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0594c4be093e48e2be771c70bd3c6162
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…