Dimethylformamide → HCID 67236723, compound

HRID 1505370Notes

Reaction equation

HRID 1505370 reaction equation
Cl[C:2]1C=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[CH3:20])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C[N:29](C)C=O>>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([O:21][C:2]2[N:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][N:29]=2)[CH:17]=[CH:18][C:19]=1[CH3:20])[CH3:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 21908691HCID 21908691, compound2×

Product 1

HCID 67236723HCID 67236723, compound

Procedure

2-chloro-5-nitropyridine (114 mg, 0.716 mmol, 1 equiv) was dissolved in 3 mL of dimethylformamide. 3-(ethyloxy)-4-methylphenol (Intermediate 90, 109 mg) and potassium carbonate (198 mg, 1.432 mmol) were added. The reaction mixture was stirred at room temperature 3 hours. The reaction mixture was filtered. The filtrated solid was washed with dichloromethane. The volatiles were evaporated under vacuum. Ethyl acetate and brine were added to the residue. The compound was extracted 2 times with ethyl acetate and 2 times with dichloromethane. The gathered organic phases were dried over sodium sulphate, filtered and evaporated to afford the title compound which was used directly in the next step (113 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe filtrated solid was washed with dichloromethane
  3. customThe volatiles were evaporated under vacuum
  4. additionEthyl acetate and brine were added to the residue
  5. extractionThe compound was extracted 2 times with ethyl acetate and 2 times with dichloromethane
  6. dry with materialThe gathered organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-fd5b66e41b29425dafa8bdb8f692b825
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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