Ammonium Hydroxide → 4-(4-aminophenyl)-1H-pyrrole-3-carboxamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15]CC)=O)=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[NH4+:19]>C(OCC)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([NH2:19])=[O:15])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 0.07 g (0.304 mmol) of ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylate in 10 cm3 of a 22% aqueous ammonium hydroxide solution is heated in an autoclave at a temperature in the region of 80° C. for 84 hours. After stopping the heating and then returning to ambient temperature and pressure, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give an orange solid which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (98/1/1 by volume)]. After concentrating the fractions under reduced pressure, a residue is obtained which is stirred in 10 cm3 of diethyl ether and then filtered and dried under reduced pressure (2.7 kPa) to give 0.02 g of 4-(4-aminophenyl)-1H-pyrrole-3-carboxamide, in the form of a brown solid: EI: m/z=201 (M+) base peak, m/z=185 (M−NH2+), m/z=157 (M-CONH2+).
Workup
- customthen returning to ambient temperature
- concentrationpressure, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
- customto give an orange solid which
- customis purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (98/1/1 by volume)]
- concentrationAfter concentrating the fractions under reduced pressure
- customa residue is obtained which
- filtrationfiltered
- customdried under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-f19f91335b8d43d78963a6916eb2069f
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592365B2
Reaction notes
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