Diethyl (ethoxymethylene)malonate → HCID 178469614, compound

HRID 2289922Notes

Reaction equation

HRID 2289922 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].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:6]2[C:4](=[CH:3][C:2]([I:1])=[CH:8][CH:7]=2)[N:5]=[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 122713-Iodoaniline

Product 1

HCID 178469614HCID 178469614, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Iodoaniline (8.50 mL) and diethyl ethoxymethylenemalonate (14.30 mL) are heated at 130° C. for 1 hour. The reaction is cooled to room temperature and 70 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 filtered, washed with hexanes, and dried. The solid is triturated in ethyl acetate to give 12.82 g of ethyl 4-hydroxy-7-iodoquinoline-3-carboxylate. A mixture of this ester (0.35 g) and 4-chlorobenzylamine (3.0 mL) are heated at 180° C. for 1 hour. The reaction is cooled to 70° C. and poured into 50 mL diethyl ether. A tan solid which crystallizes slowly out of diethyl ether is obtained. The solid is recrystallized from ethyl acetate/hexanes to give the desired product (0.22 g).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationthe resulting solid filtered
  3. washwashed with hexanes
  4. customdried
  5. customThe solid is triturated in ethyl acetate

Sources & evidence

ORD record
ord-436bd966023e4fd3b7deb97a1c033e87
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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