Diethyl (ethoxymethylene)malonate → HCID 178469653, compound

HRID 1068022Notes

Reaction equation

HRID 1068022 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].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>[OH:11][C:12]1[C:5]2[C:3](=[C:2]([I:1])[CH:8]=[CH:7][CH:6]=2)[N:4]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 119952-Iodoaniline

Product 1

HCID 178469653HCID 178469653, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 2-iodoaniline (8.22 g) and diethyl ethoxymethylenemalonate (8.00 mL) is heated at 130° C. for 1 h. The reaction is cooled to room temperature. Diphenyl ether (100 mL) is added and the reaction is heated at 250° C. for 1.25 h. The reaction is cooled to room temperature and the resulting solid is filtered, washed thoroughly with hexanes, and dried to give ethyl 4-hydroxy-8-iodo-3-quinolinecarboxylate (6.84 g).

Workup

  1. temperaturethe reaction is heated at 250° C. for 1.25 h
  2. temperatureThe reaction is cooled to room temperature
  3. filtrationthe resulting solid is filtered
  4. washwashed thoroughly with hexanes
  5. customdried

Sources & evidence

ORD record
ord-6723a32f18d7425dad7e38485a00ee1e
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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