Triethylamine → HCID 21913181, compound

HRID 1008067Notes

Reaction equation

HRID 1008067 reaction equation
C(N(CC)CC)C.[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.[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>CN(C)C=O>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 21913181HCID 21913181, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (18.9 g, 136 mmol) was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (25 g, 113 mmol) in N,N-dimethylformamide (100 mL). 4-Aminobutan-1-ol (11.1 g, 124. mmol) was added with a syringe and the reaction mixture was allowed to stir under a nitrogen atmosphere at ambient temperature for 17 hours. A portion (85 mL) of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (200 mL), washed with water (2×50 mL) then with brine (75 mL), dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide a solid. This material was recrystallized from ethyl acetate/hexanes to provide 15.07 g of 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butan-1-ol as yellow powder. An additional 5.70 g was isolated from the mother liquor.

Workup

  1. customA portion (85 mL) of the solvent was removed under reduced pressure
  2. additionThe residue was diluted with ethyl acetate (200 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialwith brine (75 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a solid
  8. customThis material was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ef54515a5ce64170afd103f6e2ea3721
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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