1,4-Cyclohexadiene → N-(4-Fluorophenyl)-N'-(4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide

HRID 1924159Notes

Reaction equation

HRID 1924159 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]CC4C=CC=CC=4)=[CH:19][CH:18]=3)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C1CC=CCC=1>CCO.[Pd]>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14]([C:11]2([C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:10])[CH2:13][CH2:12]2)=[O:15])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 57810288Cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-phenyl)-amide (4-fluoro-phenyl)-amide

Product 1

HCID 57810197N-(4-Fluorophenyl)-N'-(4-hydroxyphenyl)cyclopropane-1,1-dicarboxamideYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing mixture of cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-phenyl)-amide (4-fluoro-phenyl)-amide (46 g, 113 mmol), 10% Pd/C (2 g) in EtOH (400 mL) was added dropwise 1,4-cyclohexadiene (62.7 mL, 678 mmol). Stirring was continued for 2-5 h until the reaction was complete. The mixture was cooled to rt, filtered through celite, and washed with EtOH. The solution was then concentrated under reduced pressure. To the flask containing the crude product was added CHCl3 (200 mL). The resulting suspension was stirred for 15 min at it. The solid was filtered, and dried in the air to give cyclopropane-1,1-dicarboxylic acid (4-fluoro-phenyl)-amide (4-hydroxy-phenyl)-amide (34.4 g, 95%, yield).

Workup

  1. filtrationfiltered through celite
  2. washwashed with EtOH
  3. concentrationThe solution was then concentrated under reduced pressure
  4. additionTo the flask containing the crude product
  5. additionwas added CHCl3 (200 mL)
  6. stirringThe resulting suspension was stirred for 15 min at it
  7. filtrationThe solid was filtered
  8. customdried in the air

Sources & evidence

ORD record
ord-5f7a398147c44e97bc31e5ab75da4fab
Source dataset
uspto-grants-2012_05
Patent number
US08178532B2

Reaction notes

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