Water → HCID 10308853, compound

HRID 1793932Notes

Reaction equation

HRID 1793932 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)(=O)C>C1COCC1>[NH2:5][CH2:4][C:3]1[C:2]([NH2:1])=[N:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:6]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 3353880HCID 3353880, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10308853HCID 10308853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of argon, a solution of 2-amino-4-(2,4-dichloro-phenyl)-6-phenyl-nicotinonitrile (580 mg, 1.71 mmol) in THF (2 ml) is added slowly to a suspension of LiAlH4 (324 mg, 8.52 mmol) in THF (2 ml). After stirring for 2 h at room temperature, the reaction mixture is cooled to −20° C. and water (0.4 ml) is added. After 15 min, ethyl acetate is added and the mixture is filtered through Decalite. The organic phase is then separated, washed with water, and dried over sodium sulfate. Purification by flash chromatography (silica gel, methanol, dichloromethane) affords the title compound, MS: m/e=343.8 (M+H+), as a light yellow solid (36 mg, 6%).

Workup

  1. temperaturethe reaction mixture is cooled to −20° C.
  2. waitAfter 15 min
  3. filtrationthe mixture is filtered through Decalite
  4. customThe organic phase is then separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customPurification by flash chromatography (silica gel, methanol, dichloromethane)

Sources & evidence

ORD record
ord-cfce48453a114e55b176abcc0e26f29c
Source dataset
uspto-grants-2006_04
Patent number
US07022718B2

Reaction notes

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