Toluene → HCID 58762517, compound

HRID 858853Notes

Reaction equation

HRID 858853 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][C:20]2([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[O:25][C:24](=[O:26])C(=[N+]=[N-])[C:22](=[O:29])[CH2:21]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[C:35]1(C)C=CC=CC=1>C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[Cl:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][C:20]2([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[O:25][C:24](=[O:26])[C:1]([N:2]([CH3:35])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:22]([OH:29])[CH2:21]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7515N-MethylanilineHCID 58762625HCID 58762625, compound

Product 1

HCID 58762517HCID 58762517, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 21674Acetic acid, rhodium(2+) saltCatalyst

Procedure

To a refluxing solution of N-methylaniline (0.115 mL, 1.1 mmol) and rhodium (II) acetate (9.4 mg) in toluene (1.6 mL) was added 6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-3-diazo-dihydro-pyran-2,4-dione (0.080 g, 0.213 mmol) from Step 1 below over 1 hour. The reaction was stirred at reflux for three more hours. The reaction was concentrated by rotary evaporation, and then purified by preparatory HPLC to give the desired product (28 mg, 29% yield).

Workup

  1. temperatureat reflux for three more hours
  2. concentrationThe reaction was concentrated by rotary evaporation
  3. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-fb07ca46699c47539ef8f8021f9affee
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…