Pyrrolidine → HCID 22641468, compound
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([NH2:14])[CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)(C)C>[ClH:1].[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:3][C:4]([NH2:14])=[N:5]2)=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 319 mg (0.92 mmol) of 4-chloro-7-methoxy-quinolin-2-ylamine in 20 ml of isopropanol was treated with 130 mg (1.83 mmol) of pyrrolidine and heated at 60° C. for 6 h. The reaction mixture was cooled to RT, concentrated in vacuo. The residue was applied to a silica gel column with hexane/AcOEt (1:1) as eluent. The purified fractions were combined and concentrated in vacuo upon which the desired product crystallized out. The crystals were filtered off and dried in a high vacuum to give 48 mg (21%) of 7-methoxy-4-pyrrolidin-1-yl-quinolin-2-ylamine hydrochloride as a light brown solid. EI mass spectrum, m/e: 243.2 (M calculated for C14H17N3O: 243).