Sodium Hydroxide → HCID 57845538, compound
Reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].[OH-:18].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[C:6]=1[C:7]([NH2:8])=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 0.26 g (1.139 mmol) of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carbonitrile in 5 cm3 of concentrated sulphuric acid is heated at a temperature in the region of 80° C. for 1 hour. After having cooled the reaction mixture to a temperature in the region of 20° C., it is poured over crushed ice and then a 5N aqueous sodium hydroxide solution is slowly added to a basic pH in the region of 10. The reaction mixture is extracted with 7 times 10 cm3 of a dichloromethane/MeOH mixture (98/2 by volume). All the organic phases are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.19 g of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide, in the form of a red-brown solid; EI: m/z=246 (M+) base peak, m/z=229 (M−NH3+).
Workup
- temperatureAfter having cooled the reaction mixture to a temperature in the region of 20° C., it
- additionis poured
- customover crushed ice
- extractionThe reaction mixture is extracted with 7 times 10 cm3 of a dichloromethane/MeOH mixture (98/2 by volume)
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-dda66af48bfa4defa3c9f10e707bc4a6
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592365B2
Reaction notes
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