Aniline → HCID 178469510, compound

HRID 1829156Notes

Reaction equation

HRID 1829156 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[OH:13][C:11]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

3

Reactant 2

HCID 6115AnilineHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 178469510HCID 178469510, compoundYield 44.1%

Conditions

Temperature
200 °C

Procedure

Diethyl ethoxymethylenemalonate (115 g) was dropwise added to aniline (50 g), and the mixture was refluxed for 1 hr. The resulting ethanol was evaporated under atmospheric pressure, and the residue was heated at 200° C. and poured into diphenyl ether (750 mL). The mixture was stirred at 220–250° C. for 2 hr with heating. The resulting ethanol was again evaporated under atmospheric pressure, and the reaction mixture was allowed to cool to room temperature. The precipitated solid was collected by filtration and washed with hexane to give ethyl 4-hydroxyquinoline-3-carboxylate (51.0 g) as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 1 hr
  2. customThe resulting ethanol was evaporated under atmospheric pressure
  3. additionpoured into diphenyl ether (750 mL)
  4. temperaturewith heating
  5. customThe resulting ethanol was again evaporated under atmospheric pressure
  6. temperatureto cool to room temperature
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with hexane

Sources & evidence

ORD record
ord-6c71d3a87239426ebdb17165a9c9c2cc
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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