Diethyl (ethoxymethylene)malonate → HCID 178469677, compound

HRID 358886Notes

Reaction equation

HRID 358886 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.[F:16][C:17]1[C:18]([O:25][CH3:26])=[C:19]([CH:21]=[CH:22][C:23]=1[F:24])[NH2:20].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[F:24][C:23]1[CH:22]=[C:21]2[C:19](=[C:18]([O:25][CH3:26])[C:17]=1[F:16])[N:20]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]2[OH:13]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 111374253,4-Difluoro-2-methoxyaniline

Product 1

HCID 178469677HCID 178469677, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2.84 g (0.013 mole) of diethyl ethoxymethylenemalonate were added to 1.74 g (0.011 mole) of 3,4-difluoro-2-methoxyaniline (VIII) (prepared as described in Preparation 13). The mixture was then stirred at 140°-150° C. for 3 hours, after which 20 ml of diphenyl ether were added, and the mixture was stirred at 240°-250° C. for 1 hour. At the end of this time, the mixture was allowed to cool to room temperature, and then hexane was added to precipitate crystals, which were collected by filtration. 1.60 g of ethyl 6,7-difluoro-4-hydroxy-8-methoxyquinoline-3-carboxylate (IX) were obtained as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 240°-250° C. for 1 hour
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3f4930b859e14315b940317b9c299aef
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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