Potassium Carbonate → 4-(4-Amino-3-nitro-phenoxy)-pyridine-2-carboxylic acid dimethylamide

HRID 13522

Reaction equation

HRID 13522 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:22][N:23]([CH3:33])[C:24]([C:26]1[CH:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][N:23]([CH3:33])[C:24]([C:26]1[CH:31]=[C:30]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH:29]=[CH:28][N:27]=1)=[O:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 37588824-Amino-3-NitrophenolHCID 49622524-chloro-N,N-dimethylpyridine-2-carboxamide

Product 1

HCID 210372944-(4-Amino-3-nitro-phenoxy)-pyridine-2-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added 4-Chloro-pyridine-2-carboxylic acid dimethylamide (1 eq) and potassium carbonate (1.2 eq) and then it was stirred at 90° C. for 3 days. The reaction mixture was then concentrated before partitioning between ethyl acetate and water. The organic layer was separated, washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification by flash chromatography with ethyl acetate and hexane (1:1) gave the desired product as a yellow syrup. HPLC, 1.69 min; MS: MH+=303.1.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custombefore partitioning between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification by flash chromatography with ethyl acetate and hexane (1:1)

Sources & evidence

ORD record
ord-2ce32362d15346048dc575b0b0923ee7
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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