Diethyl (ethoxymethylene)malonate → HCID 178469646, compound

HRID 2289920Notes

Reaction equation

HRID 2289920 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]2[C:3]=1[N:4]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]2[OH:12]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 679842-Fluoro-4-methylaniline

Product 1

HCID 178469646HCID 178469646, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

A mixture of 2-fluoro-4-methylaniline (5.0 g) and diethyl ethoxymethylene-malonate (8.64 g) is heated to 130° C. for 2 h with removal of ethanol by a Dean-Stark trap. The mixture is cooled to 75° C. and diphenyl ether (50 mL) is added. The solution is heated to 250° C. for 2 h with removal of ethanol by a Dean-Stark trap, then cooled to room temperature. The resulting solid is collected, washed with hexanes and dried to yield 5.564 g of ethyl 8-fluoro-4-hydroxy-6-methylquinoline-3-carboxylate. A mixture of this ester (0.50 g) and 4-chlorobenzylamine (3.0 mL) are heated at 180° C. for 1 hour. The reaction is cooled and poured into 50 mL of diethyl ether. The resulting solid is filtered, dried, and purified by trituration in acetone to give the desired product (0.54 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting solid is collected
  3. washwashed with hexanes
  4. customdried

Sources & evidence

ORD record
ord-9c5ce9b58509476683bd342b47320fdd
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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