Water → HCID 67608342, compound

HRID 925288Notes

Reaction equation

HRID 925288 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 135867984-Methoxy[2,2′-bipyridine]-6-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 67608342HCID 67608342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Over a solution of 4-Methoxy-[2,2′]bipyridinyl-6-carbonitrile (5.0 g, 23.7 mmol) in tetrahydrofuran (25 mL), a 1.0 M solution of LiAlH4 in tetrahydrofuran (75 mL, 75.0 mmol) was slowly added and the reaction mixture was stirred for 2 h at 25° C. The reaction was then cooled to 0° C., water (2.5 mL) followed by a 15% aqueous solution of NaOH (2.5 mL) were slowly added and stirred at 25° C. for 16 hours. The reaction mixture was filtered through celite, washed with tetrahydrofuran and the organic solvent removed under reduced pressure. The aqueous residue was extracted with dichloromethane, the organic solvent dried with sodium sulphate anhydrous, filtered and removed under reduced pressure to afford C-(4-Methoxy-[2,2′]bipyridinyl-6-yl)-methylamine as an orange oil (3.5 g, aprox 68%) that was used in the next step without purification.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. additionwere slowly added
  3. stirringstirred at 25° C. for 16 hours
  4. filtrationThe reaction mixture was filtered through celite
  5. washwashed with tetrahydrofuran
  6. customthe organic solvent removed under reduced pressure
  7. extractionThe aqueous residue was extracted with dichloromethane
  8. dry with materialthe organic solvent dried with sodium sulphate anhydrous
  9. filtrationfiltered
  10. customremoved under reduced pressure

Sources & evidence

ORD record
ord-8a1f380a632a42ebb0ed3d57bdce8740
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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