p-Toluenesulfonic acid → 5-Methyl-1-(3-nitrobenzyl)-2-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

HRID 413914

Reaction equation

HRID 413914 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])([O-:4])=[O:3].C(=O)(O)[O-].[Na+].[N+](C1C=C(C=CC=1)CN)([O-])=O.[CH2:29]([O:31][C:32](=[O:46])[CH:33]([C:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:34][C:35](=O)[CH3:36])[CH3:30].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:29]([O:31][C:32]([C:33]1[CH:34]=[C:35]([CH3:36])[N:9]([CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)[C:38]=1[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:46])[CH3:30]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 1227223-NitrobenzylamineHCID 516892Sodium BicarbonateHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)HCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 101093645-Methyl-1-(3-nitrobenzyl)-2-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

m-Nitrobenzylamine hydrochloride (3 g) was suspended in an aqueous solution of saturated sodium bicarbonate (30 mL), and extracted with chloroform. The organic layer was dried over MGSO4, the solids saturated and solvents removed under vacuum to yield the free base. The m-nitrobenzylamine (5 mmol, 0.8 g) prepared above, 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid were combined in ethanol, then heated under reflux. The resulting residue was purified over silica gel to yield the named product, 1H-NMR (CDCl3, ppm): 1.10 t (3H), 3.16 s (3H), 4.08 q (2H), 5.04 s (2H), 6.55 s (1H), 7.07-7.53 bm (7H), 7.72 bs (1H), 8.04 bd (1H).

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer was dried over MGSO4
  3. customthe solids saturated and solvents removed under vacuum
  4. customto yield the free base
  5. temperatureheated
  6. temperatureunder reflux
  7. customThe resulting residue was purified over silica gel
  8. customto yield the named product, 1H-NMR (CDCl3, ppm): 1.10 t (3H), 3.16 s (3H), 4.08 q (2H), 5.04 s (2H), 6.55 s (1H), 7.07-7.53 bm (7H), 7.72 bs (1H), 8.04 bd (1H)

Sources & evidence

ORD record
ord-c9efedc6a36749e2a470569d83e999da
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Linked notes

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