Water → 2,2-Dimethyl-N-(5-nitro-2-pyridinyl)propanamide

HRID 1039101Notes

Reaction equation

HRID 1039101 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:11][C:12]([CH3:17])([CH3:16])[C:13](Cl)=[O:14].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:11][C:12]([CH3:17])([CH3:16])[C:13]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 32494522,2-Dimethyl-N-(5-nitro-2-pyridinyl)propanamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-nitropyridin-2-amine (0.5 g, 3.59 mmol) was slurried in DCM (12 ml). TEA (2.5 ml, 18 mmol) and DMAP (88 mg, 0.72 mmol) were added. 2,2-dimethylpropanoyl chloride was added prop wise and the mixture stirred at RT overnight. The mixture was diluted into water (30 ml):saturated sodium bicarbonate (aq, 10 ml), extracted with DCM (3×30 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered, and the volatiles removed in vacuum. The material was purified by chromatography on SiO2 eluting with 10% acetone: hexanes to give the titled compound.

Workup

  1. extractionsaturated sodium bicarbonate (aq, 10 ml), extracted with DCM (3×30 ml)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuum
  6. customThe material was purified by chromatography on SiO2 eluting with 10% acetone

Sources & evidence

ORD record
ord-0a255d4b08b14be8b9115ed5a4c17430
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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