Dimethylformamide → HCID 67415424, compound

HRID 2366783Notes

Reaction equation

HRID 2366783 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[CH:16][C:17]=1[F:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[F:18][C:17]1[CH:16]=[CH:15][C:14]([O:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:13][C:12]=1[NH2:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 67415424HCID 67415424, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-5-nitropyridine (6.34 g, 40 mmol), 3-amino-4-fluorophenol (5.08 g, 40 mmol), potassium carbonate (5.52 g, 40 mmol) and N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The reaction mixture was poured into water (200 mL), and the Mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was to concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50), and crystallized from diethyl ether to give the title compound (7.90 g, 79%) as a yellow powder.

Workup

  1. extractionthe Mixture was extracted with ethyl acetate (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationto concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50)
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-15608e30a3074b4a8b60e54d909ecf5d
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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