Ammonium Chloride → HCID 53713758, compound

HRID 249987Notes

Reaction equation

HRID 249987 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8](OC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(OCC)C.O>[CH3:1][S:2][C:3]1[CH:12]=[C:7]([CH2:8][OH:9])[CH:6]=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 12782772HCID 12782772, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53713758HCID 53713758, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl 5-methylsulphanylnicotinate (916 mg, 5 mmol) is dissolved in 150 mL of diethyl ether, admixed at 0° C. with lithium aluminium hydride (660 mg, 18 mmol) and subsequently stirred at room temperature for 90 minutes. The reaction is discontinued by addition of 10% ammonium chloride solution at 0° C. The batch is diluted with water and the aqueous phase is extracted with ether. Drying of the organic phase over sodium sulphate, concentrating the solvent and also chromatographic purification of the residue (silica gel, n-hexane/ethyl acetate: 50→100% ethyl acetate) gives the desired product in 7% yield (50 mg).

Workup

  1. extractionthe aqueous phase is extracted with ether
  2. dry with materialDrying of the organic phase over sodium sulphate
  3. concentrationconcentrating
  4. customthe solvent and also chromatographic purification of the residue (silica gel, n-hexane/ethyl acetate: 50→100% ethyl acetate)

Sources & evidence

ORD record
ord-357f3124678a4c5495a2f53f72e8c1f8
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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