Ethyl benzoylacetate → HCID 86250556, compound

HRID 370464Notes

Reaction equation

HRID 370464 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:14]([CH2:22][C:23](OCC)=[O:24])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:14]([CH2:22][C:23]([NH:1][C:2]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:24])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 1515287ethyl 2-amino-5-chlorobenzoate

Product 1

HCID 86250556HCID 86250556, compoundYield 49.1%

Procedure

To 6.0 grams of ethyl 2-amino-5-chlorobenzoate is added 6.4 grams of ethyl benzoylacetate, the mixture is heated at 180° to 190° C. for ten hours, cooled, crystals separated out therefrom are collected by filtration, and washed with methanol to give 5.1 grams of ethyl 2-benzoylacetylamino-5-chlorobenzoate, colorless needles. To 200 ml of ethanol is added 640 mg of metal sodium, then 4.8 grams of ethyl 2-benzoylacetylamino-5-chlorobenzoate is added thereto, the mixture is heated to reflux for two hours, cooled, poured into ice water, adjusted to pH 3 with 10% hydrochloric acid, crystals separated out therefrom are collected by filtration, and recystallized from dimethylformamide and methanol to give 1.9 grams of 3-benzoyl-6-chloro-4-hydroxy-2-quinoline, pale yellow needles, melting at above 300° C.

Workup

  1. temperaturethe mixture is heated at 180° to 190° C. for ten hours
  2. temperaturecooled
  3. customcrystals separated out
  4. filtrationtherefrom are collected by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-059d9ad078cf40d7a08c0f07e4cf1142
Source dataset
uspto-grants-1985_07
Patent number
US04526894

Reaction notes

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