Water → HCID 86641408, compound

HRID 1512190Notes

Reaction equation

HRID 1512190 reaction equation
O[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2.[Cl:16][C:17]1[CH:22]=[C:21]([N+]([O-])=O)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-:27].[K+].[K+].O>CS(C)=O>[Cl:16][C:17]1[CH:22]=[C:21]([O:27][C:6]2[CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[C:9]3[C:4]([CH:5]=2)=[CH:3][CH:2]=[CH:11][CH:10]=3)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7351522-Chloro-4-nitropyridineHCID 11367671Methyl 6-hydroxy-1-naphthoate

Product 1

HCID 86641408HCID 86641408, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 6-hydroxy-1-naphthalenecarboxylic acid, methyl ester (0.202 g, 1.0 mmol), 2-chloro-4-nitropyridine (0.174 mg, 1.1 mmol) and potassium carbonate (0.276 g, 2 mmol) in dimethylsulphoxide (5 mL) is heated at 70° C. for 1 h. The mixture is poured into water and the crude product is filtered off, washed with water. The crude product is dissolved in ethyl acetate, washed with brine, dried (Na2SO4) and the solvent is evaporated off under reduced pressure to give a residue which is recrystallized from ethylacetate-hexane to afford the title compound as a beige crystalline solid, m.p.: 103-104° C.

Workup

  1. filtrationthe crude product is filtered off
  2. washwashed with water
  3. dissolutionThe crude product is dissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give a residue which
  8. customis recrystallized from ethylacetate-hexane

Sources & evidence

ORD record
ord-e017078d9ae344d187c8f040140a65e4
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

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