Methyl Ethyl Ketone → HCID 15917386, compound

HRID 1758139Notes

Reaction equation

HRID 1758139 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][CH:7]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>CCCCCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 15917385HCID 15917385, compound

Product 1

HCID 15917386HCID 15917386, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A mixture of 1.5 grams (0.0068 mole) 2-(5-chloropyridin-2-yloxy)phenol, 1.3 grams 2-chloro-5-nitropyridine, 1.0 grams potassium carbonate, and 40 ml of methyl ethyl ketone was heated at reflux overnight. Excess water was added and the aqueous mixture extracted with 200 ml of ethyl ether. The ether extract was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and the solvent was evaporated to yield a solid which was suspended in hexane and filtered. Yield 1.4 grams, m.p. 82°-84°; ir (Nujol): 6.15, 6.25 (C=N, NO2), 13.30 (broad), 13.70 microns; NMR (CDCl3): δ6.55 (s, ArH), 6.75 (d, ArH), 6.95 (s, ArH), 7.35 (s, 4H, ArH), 7.40-7.65 (m, ArH), 8.05 (d, ArH), 8.40 (AB quartet, ArH), 8.95 (d, ArH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe aqueous mixture extracted with 200 ml of ethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto yield a solid which
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5643838a8404401792cf6a0047268d03
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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