Potassium Carbonate → N-(3-nitro-5-(2-oxopyridin-1(2H)-yl)phenyl)acetamide

HRID 64138Notes

Reaction equation

HRID 64138 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([N:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=[O:21])[CH:7]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamideHCID 178516071HCID 178516071, compound

Product 1

HCID 117777577N-(3-nitro-5-(2-oxopyridin-1(2H)-yl)phenyl)acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-bromo-5-nitrophenyl)acetamide (1 g, 3.85 mmol), pyridin-2-ol (0.4 g, 4.24 mmol, 1.1 eq.), potassium carbonate (1 g, 1.3 mmol, 1.0 eq.) and copper(I) iodide (10 mg) in toluene (20 ml) was added trans cyclohexyl diamine (5 mg, 0.039 mmol, 0.01 eq.) and the mixture was heated at 100° C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 95% yield (1 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane)
  5. customto give the product in 95% yield (1 g)

Sources & evidence

ORD record
ord-3f289cb8667f4e2a94c23e7318ba3a20
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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