Ethyl 2-methylacetoacetate → HCID 178488806, compound

HRID 2270085Notes

Reaction equation

HRID 2270085 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH3:10][CH:11]([C:17]([CH3:19])=O)[C:12](OCC)=[O:13].C1(C)C=CC=CC=1>Cl.C1(C)C=CC=CC=1.O>[CH3:19][C:17]1[C:11]([CH3:10])=[C:12]([OH:13])[C:6]2[C:4](=[C:3]([O:2][CH3:1])[CH:9]=[CH:8][CH:7]=2)[N:5]=1

Participants

6

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 1140TolueneHCID 70002-Methoxyaniline

Product 1

HCID 178488806HCID 178488806, compoundYield 10.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 22272177Toluene waterSolvent

Conditions

Temperature
200 °C

Procedure

12.3 g of 2-methoxyaniline, 14.2 g of ethyl 2-methylacetoacetate and 3 drops of 1N HCl are introduced into a 250 ml three-necked flask fitted with Dean-Stark apparatus and a condenser. The mixture is stirred overnight. 100 ml of toluene are added and the mixture is refluxed until distillation of the toluene/water azeotrope is complete. The toluene is then evaporated off and 100 ml of diphenyl ether are added. The mixture is heated at 200° C. for 1 h. 50 ml of diphenyl ether are evaporated off and the mixture is cooled to room temperature. 20 ml of petroleum ether are added and the product which crystallizes is filtered off. 2.1 g (yield: 10%) of 2,3-dimethyl-4-hydroxy-8-methoxyquinoline are obtained—m.p.: >290° C.

Workup

  1. customfitted with Dean-Stark apparatus and a condenser
  2. customThe toluene is then evaporated off
  3. addition100 ml of diphenyl ether are added
  4. custom50 ml of diphenyl ether are evaporated off
  5. temperaturethe mixture is cooled to room temperature
  6. addition20 ml of petroleum ether are added
  7. customthe product which crystallizes
  8. filtrationis filtered off

Sources & evidence

ORD record
ord-07cc7efa94374e1795158f9f7cc54e79
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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