Ethyl 3-chloro-3-oxopropionate → 6-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1745857Notes

Reaction equation

HRID 1745857 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:6]([CH:13]=1)[C:7](N(OC)C)=[O:8].[CH2:24]([O:26][C:27](=[O:32])[CH2:28][C:29](Cl)=[O:30])[CH3:25].CC[O-].[Na+]>C1C=CC=CC=1.O>[CH2:24]([O:26][C:27]([C:28]1[C:29](=[O:30])[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:5]2[C:6]([C:7]=1[OH:8])=[CH:13][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:32])[CH3:25]

Participants

6

Reactant 3

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 2723922Sodium ethoxideHCID 222266005-chloro-N-methoxy-2-(4-methoxy-benzylamino)-N-methyl-benzamide

Product 1

HCID 546885376-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl esterYield 42,749.801%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 9 (0.13 g, 0.38 mmol) in 3 mL of anhydrous benzene was treated with ethyl-3-chloro-3-oxopropionate (54 μL, 63.0 mg, 0.421 mmol). The reaction mixture was heated to 80° C. for 1 h. The reaction was allowed to cool to room temperature and was concentrated in vacuo. The resulting oil was dissolved in 3 mL of ethanol, treated with NaOEt (40.0 mg, 0.59 mmol). The suspension was heated to 80° C. for 10 min, allowed to cool to room temperature, and diluted with H2O. The resulting precipitate was filtered to give 10 (63.0 g, 43%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe resulting oil was dissolved in 3 mL of ethanol
  4. temperatureThe suspension was heated to 80° C. for 10 min
  5. temperatureto cool to room temperature
  6. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-45b995454dc34d469cd0b5c55c4e7183
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

Loading…