Diethyl (ethoxymethylene)malonate → HCID 178469563, compound

HRID 1067940Notes

Reaction equation

HRID 1067940 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O:11][CH:12]=[C:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C>[OH:11][C:12]1[C:7]2[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:8]=2)[N:6]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 108934-Iodoaniline

Product 1

HCID 178469563HCID 178469563, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Iodoaniline (8.60 g) and diethyl ethoxymethylenemalonate (7.90 mL) are heated at 130° C. for 1 hour. The reaction is cooled to room temperature and 60 mL diphenyl ether is added. The solution is heated at 250° C. for 1.5 hours with removal of ethanol by a Dean-Stark trap. The reaction is cooled to room temperature and the resulting solid is filtered, washed with hexanes, and dried to yield 11.20 g of ethyl 4-hydroxy-6-iodoquinoline-3-carboxylate. A mixture of this ester (0.58 g) and 4chlorobenzylamine (4.0 mL) are heated at 180° C. for 1.5 hours. The reaction is cooled and poured into 50 mL diethyl ether. The resulting solid is filtered, triturated in ethyl acetate, and filtered again to give the desired product (0.50 g).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationthe resulting solid is filtered
  3. washwashed with hexanes
  4. customdried

Sources & evidence

ORD record
ord-f59fcbef5a2d4789bba9aca64ef541ec
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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