Methyl Salicylate → HCID 9250987, compound

HRID 2399277Notes

Reaction equation

HRID 2399277 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 9250987HCID 9250987, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl salicylate (1.7 mL, 0.0131 mol), 1-chloro-2-nitrobenzene (2.30 mL, 0.01965 mol) and potassium carbonate (3.62 g, 0.0262 mol) were mixed in dimethylformamide (35 mL), under argon, at 150° C. for 16 h. The solvent was evaporated and the crude material was flash chromatographed (silica gel, ethyl acetate/hexane). Concentration in vacuo yielded the title compound. 1H NMR (250 MHz, CDCl3) δ8.0 (m, 4H), 7.58 (m, 1H), 7.35 (m, 1H), 7.23 (m, 1H), 7.13 (dd, 1H), 6.85 (dd, 2H).

Workup

  1. customThe solvent was evaporated
  2. customchromatographed (silica gel, ethyl acetate/hexane)
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-11314236eab64891bef81af358e843c9
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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