Formamide → 5-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 384305Notes

Reaction equation

HRID 384305 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:13]=2[O:21][CH3:22])[N:8]([CH3:23])[C:7]=1[CH3:24])=[O:5])[CH3:2].C(N)=O>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=2[O:21][CH3:22])[N:8]([CH3:23])[C:7]=1[CH3:24])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 713FormamideHCID 596156595-(3-nitro-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 596156885-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitro-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6f (300 mg, 0.9 mmol) was dissolved in 5 mL of ethyl acetate followed by addition of formamide (227 mg, 1.61 mmol) and 60 mg of palladium on carbon. The reaction mixture was heated to reflux for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain the title compound 5-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6g (234 mg, yield 86%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c87bf086ddfb4a22bb6200dcaf648899
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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