Aluminium lithium hydride → HCID 23445111, compound

HRID 433598Notes

Reaction equation

HRID 433598 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH:13]=[N:12][CH:11]=1>C1COCC1>[Cl:23][C:18]1[CH:17]=[C:16]([C:14]2[CH:15]=[C:10]([CH2:9][OH:8])[CH:11]=[N:12][CH:13]=2)[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69041910HCID 69041910, compound

Product 1

HCID 23445111HCID 23445111, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (161 mg, 4.2 mmol) in THF (20 ml) at 0° C. was added dropwise 5-(3,4-dichloro-phenyl)-nicotinic acid methyl ester (2.0 g, 7.0 mmol) in THF (20 ml) and stirred for a further 2 h at this temperature. The reaction was quenched by careful addition of THF/H2O (9:1) and then dried directly with Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed [silica, elution with CH2Cl2/(2M NH3 MeOH)=97:3] to afford the title compound (480 mg, 27%) as an orange solid. MS: m/e=254.0 (M+H+).

Workup

  1. customThe reaction was quenched by careful addition of THF/H2O (9:1)
  2. dry with materialdried directly with Na2SO4
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed
  6. wash[silica, elution with CH2Cl2/(2M NH3 MeOH)=97:3]

Sources & evidence

ORD record
ord-1f21ebb373064c85978870068f44fb39
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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