Water → HCID 19781588, compound

HRID 257788Notes

Reaction equation

HRID 257788 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[NH:11][C:12]1[C:17]([C:18](=O)[NH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1.O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[NH:11][C:12]1[C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 122396712-(3-chloroanilino)-3-carbamoylpyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 19781588HCID 19781588, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of lithium aluminum hydride (4.6 g, 121.2 mmoles) in tetrahydrofuran (300 ml) was heated to reflux. To this refluxing suspension, a solution of 2-(3-chloroanilino)-3-carbamoylpyridine (10.0 g, 40.4 mmole) in tetrahydrofuran (200 ml), (prepared, for example, as described in Example 3B), was slowly added dropwise. The reaction mixture was stirred for 18 hours and cooled to room temperature. Solutions of tetrahydrofuran and H2O (20 ml, 50:50), 20 ml of 10% NaOH and 20 ml of H2O were added to the reaction mixture. A white precipitate was formed and removed by filtration. Three quarters of the solvent was removed. The residue was extracted in ethyl acetate (5×100 ml) and washed with H2O. The solution was dried over MgSO4 and the MgSO4 was removed by filtration. The solvent was removed by evaporation resulting in a 10.3 g of 2-(3-chloroanilino)-3-aminomethylpyridine, as a light yellow oil, which was used without further purification.

Workup

  1. temperaturewas heated to reflux
  2. customA white precipitate was formed
  3. customremoved by filtration
  4. customThree quarters of the solvent was removed
  5. extractionThe residue was extracted in ethyl acetate (5×100 ml)
  6. washwashed with H2O
  7. dry with materialThe solution was dried over MgSO4
  8. customthe MgSO4 was removed by filtration
  9. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9dfe5241f6294a828bf5c07073839ea6
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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