Diethyl (ethoxymethylene)malonate → HCID 178469654, compound

HRID 1060591Notes

Reaction equation

HRID 1060591 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][C:3]=1[NH2:4].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:18][C:19]1[C:5]2[C:3](=[C:2]([I:1])[CH:8]=[C:7]([CH2:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[CH:6]=2)[N:4]=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 22724558HCID 22724558, compound

Product 1

HCID 178469654HCID 178469654, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-iodo-4-(tetrahydro-2H-pyran-4-ylmethyl)aniline (1.0 g) and diethyl ethoxymethylenemalonate (0.70 mL) is heated to 130° C. for 1 h. The mixture is cooled to room temperature. Diphenyl ether (20 mL) is added and the reaction is heated to 250° C. for 1 h. The mixture is cooled and the resulting solid is collected and washed with hexanes. The crude product is chromatographed (Biotage flash 40M, eluant 2% MeOH/CH2Cl2) to yield 0.80 g (58%) of ethyl 4-hydroxy-8-iodo-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxylate as a solid, m.p. 218-222° C. (dec).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. temperaturethe reaction is heated to 250° C. for 1 h
  3. temperatureThe mixture is cooled
  4. customthe resulting solid is collected
  5. washwashed with hexanes
  6. customThe crude product is chromatographed (Biotage flash 40M, eluant 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-10c0d64aa54b419d9bcd855cc6bffd12
Source dataset
uspto-grants-2003_02
Patent number
US06525049B2

Reaction notes

Loading…