4-(7-hydroxyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)benzonitrile → 4-(5H-pyrrolo[1,2-c]imidazol-7-yl)benzonitrile
Reaction equation
O[C:2]1([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1>O1CCCC1.Cl>[CH:8]1[N:7]=[CH:6][N:5]2[CH2:4][CH:3]=[C:2]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)[C:9]=12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 2.35 mmol of 4-(7-hydroxyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-benzonitrile in 5 ml of tetrahydrofuran and 10 ml of 4N HCl is stirred at 50° C. for 12 hours. The reaction mixture is cooled to room temperature, poured onto ice/4N NaOH and extracted with ethyl acetate (3×). The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60 F) as a light brown solid. Rt=4.55 (Gradient I).
Workup
- temperatureThe reaction mixture is cooled to room temperature
- additionpoured onto ice/4N NaOH
- extractionextracted with ethyl acetate (3×)
- dry with materialThe combined organic phases are dried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-8f402425b3404038b7ae087d51768354
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263615B2
Reaction notes
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