P-Anisidine → 3-(4-Methoxy-phenylamino)-benzamide

HRID 1354967Notes

Reaction equation

HRID 1354967 reaction equation
CC1C=CC(C(C2C=CC(C)=CC=2)C(=O)C(C)C)=CC=1.C([O-])([O-])=O.[K+].[K+].Cl[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH2:33])=[O:32].[CH3:37][O:38][C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:37][O:38][C:39]1[CH:45]=[CH:44][C:42]([NH:43][C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31]([NH2:33])=[O:32])=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 692543-ChlorobenzamideHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanone

Product 1

HCID 211061263-(4-Methoxy-phenylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable Schlenk flask was evacuated and backfilled with argon. The flask was charged with Pd2 dba3 (9.2 mg, 0.01 mmol, 2 mol % Pd), Ligand 1 (19 mg, 0.04 mmol, 4 mol %), K2CO3 (304 mg, 2.2 mmol), 3-chloro-benzamide (156 mg, 1.0 mmol), and 4-methoxy-aniline (148 mg, 1.2 mmol). The flask was evacuated and backfilled with argon (3×) and then capped with a rubber septum. To the flask was added t-BuOH (2.5 mL). The septum was replaced with a Teflon screwcap, the flask was sealed, and the mixture was heated to 100° C. with stirring until the starting aryl chloride was consumed by TLC analysis (20 h). The reaction was cooled to room temperature, diluted with ethyl acetate, filtered through Celite, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with EtOAc/hexanes, 8.5:1.5) to give the desired product which was re-crystallized from ethyl acetate/hexanes (14/1) to give white flaky crystals (191 mg, 79%).

Workup

  1. customAn oven-dried resealable Schlenk flask was evacuated
  2. customThe flask was evacuated
  3. customcapped with a rubber septum
  4. additionTo the flask was added t-BuOH (2.5 mL)
  5. customthe flask was sealed
  6. customwas consumed by TLC analysis (20 h)
  7. temperatureThe reaction was cooled to room temperature
  8. additiondiluted with ethyl acetate
  9. filtrationfiltered through Celite
  10. concentrationconcentrated under reduced pressure
  11. customThe crude material was purified by column chromatography on silica gel (eluting with EtOAc/hexanes, 8.5:1.5)

Sources & evidence

ORD record
ord-73f4f856166a43529494327d88d9bd11
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

Loading…