5-Aminopentan-1-ol → HCID 21913098, compound

HRID 1352559Notes

Reaction equation

HRID 1352559 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1>CN(C)C=O>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1

Participants

4

Reactant 2

HCID 756345-Aminopentan-1-olHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 21913098HCID 21913098, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-amino-1-pentanol (28.03 g, 271.4 mmol) in N,N-dimethylformamide (200 mL) was added over a period of 45 minutes to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (60.01 g, 271.4 mmol) in N,N-dimethylformamide. The reaction was stirred overnight and then the N,N-dimethylformamide was removed by vacuum distillation. The residue was dissolved in ethyl acetate (500 mL), washed with water (4×75 mL), dried over magnesium sulfate and then concentrated under reduced pressure. The crude product was dissolved in hot ethyl acetate (400 mL). Hexane was added until a clear solution was obtained then the mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration and washed with cold hexane to provide 26.87 g of 5-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]pentan-1-ol as a solid. An additional 4.41 g was isolated from the filtrate.

Workup

  1. customthe N,N-dimethylformamide was removed by vacuum distillation
  2. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  3. washwashed with water (4×75 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in hot ethyl acetate (400 mL)
  7. additionHexane was added until a clear solution
  8. customwas obtained
  9. customThe resulting precipitate was isolated by filtration
  10. washwashed with cold hexane

Sources & evidence

ORD record
ord-73aa51e0ac244034aab9c872367ae079
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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