Sodium ethoxide → 2-Amino-5-(2-naphthyl)pyrrole-3-carboxamide

HRID 416023Notes

Reaction equation

HRID 416023 reaction equation
[O-][CH2:2][CH3:3].[Na+].[CH2:5]([C:9]([NH2:11])=[O:10])[C:6]([NH2:8])=[NH:7].Cl.BrCC([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[NH2:7][C:6]1[NH:8][C:2]([C:19]2[CH:18]=[CH:17][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:3][C:5]=1[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 3084595Amidinomalonamide hydrochlorideHCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Product 1

HCID 582940172-Amino-5-(2-naphthyl)pyrrole-3-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under ice-cooling, sodium ethoxide (2.7 g, 40 mmol) was added to a suspension of malonamamidine hydrochloride (5.5 g, 40 mmol) in dehydrated ethanol (130 mL), and then the mixture was stirred for 20 minutes. 2-Bromoacetylnaphthalene (5.0 g, 20 mmol) was added thereto, and the whole was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the obtained residue was purified by silica gel column chromatography to give the title reference compound (1.5 g) as a black solid (Yield 30%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe whole was stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-47df18e4a63c4970aacb527f05a45fd8
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

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