Ethyl 2-(2-methylphenoxy)acetate → HCID 68352060, compound

HRID 2174555Notes

Reaction equation

HRID 2174555 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6]C)=O.[C:14]1([CH3:27])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][C:22](OCC)=[O:23].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[Cl:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4]([OH:6])=[C:21]([O:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:27])[C:22](=[O:23])[NH:1]2)=[CH:8][C:9]=1[I:13]

Participants

5

Reactant 3

HCID 3022879Ethyl 2-(2-methylphenoxy)acetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoate2×

Product 1

HCID 68352060HCID 68352060, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2-amino-4-chloro-5-iodobenzoate (Intermediate 2) (1 g, 3.21 mmol) and ethyl 2-(o-tolyloxy)acetate (Aldrich, 0.655 g, 3.37 mmol) were dissolved in THF (10 mL) and KHMDS 1M/THF (9.63 mL, 9.63 mmol) was added in one portion at room temperature under N2. The reaction mixture was stirred at room temperature for 1 h before quenched with MeOH and concentrated under reduced pressure. The residue was dissolved in 1N NaOH then extracted with Et2O. The aqueous extracts were acidified with 1N HCl and the resulting precipitate was collected by filtration then washed successively with water and diethyl ether to give 7-chloro-4-hydroxy-6-iodo-3-(o-tolyloxy)quinolin-2(1H)-one (1.03 g, 2.409 mmol, 75% yield) as white solid. LCMS: (M+H)+=428; Rt=2.46 min.

Workup

  1. custombefore quenched with MeOH
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1N NaOH
  4. extractionthen extracted with Et2O
  5. filtrationthe resulting precipitate was collected by filtration
  6. washthen washed successively with water and diethyl ether

Sources & evidence

ORD record
ord-6c38e50daa6045d2b03585a3a4f38cbb
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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