2-Amino-2-methyl-1-propanol → 2-(1,1-Dimethyl-2-hydroxyethylamino)-3-nitro-5-(trifluoromethyl)pyridine

HRID 1370101Notes

Reaction equation

HRID 1370101 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18]>CN(C)C=O.C(OCC)(=O)C>[CH3:19][C:16]([NH:15][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1)([CH3:20])[CH2:17][OH:18]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 700154552-(1,1-Dimethyl-2-hydroxyethylamino)-3-nitro-5-(trifluoromethyl)pyridineYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1 g) in N,N-dimethylformamide (10 mL) was added 2-amino-2-methyl-1-propanol (1.18 g) at 0° C. The mixture was stirred at room temperature for 3.5 hours under nitrogen atmosphere. The mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 2-(1,1-dimethyl-2-hydroxyethylamino)-3-nitro-5-(trifluoromethyl)pyridine (1.23 g) as a yellow oil.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c20c52a88a7411980839b7f650bd14a
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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