Ammonium Chloride → HCID 58268611, compound

HRID 1517585Notes

Reaction equation

HRID 1517585 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:22])=[N:8][N:9]([C:11]2[C:16]([CH2:17][O:18][CH:19]3[CH2:21][CH2:20]3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:10]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1.[O-2].[Mn+4].[O-2]>[CH:19]1([O:18][CH2:17][C:16]2[C:11]([N:9]3[CH:10]=[C:6]([CH:4]=[O:3])[C:7]([CH3:22])=[N:8]3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 67168298HCID 67168298, compound

Product 1

HCID 58268611HCID 58268611, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(3-cyclopropoxymethyl-pyridin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (410 mg, 1.03 mmol) in tetrahydrofuran (0.15 M) at 0° C. under nitrogen, 1.0 M lithium aluminum hydride in tetrahydrofuran (1.2 equiv) is added. The mixture is stirred at room temperature for 1 h and saturated aqueous solution of ammonium chloride is added and the aqueous layer is extracted with ethyl acetate. The organic layer is separated, dried over sodium sulfate and the solvent eliminated under reduced pressure. The crude material is dissolved in dichloromethane (14 mL) and manganese (IV) oxide (1.2 g, 13.9 mmol) is added. The mixture is stirred at room temperature overnight and then filtered through a pad of celite and the solvent is evaporated under reduced pressure. The crude is passed through a pad of silica gel (eluent: ethyl acetate and dichloromethane). The solvent is eliminated under reduced pressure to yield 90 mg of the title product. MS (m/z): 258 (M+1).

Workup

  1. extractionthe aqueous layer is extracted with ethyl acetate
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. dissolutionThe crude material is dissolved in dichloromethane (14 mL)
  5. stirringThe mixture is stirred at room temperature overnight
  6. filtrationfiltered through a pad of celite
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2dbae4b8b20c48988cd530ad5cedc66d
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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