1-Pyrrolidineethanamine → 5,7-Dichloro-2-[2-(1-pyrrolidinyl) ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline dihydrochloride

HRID 326664Notes

Reaction equation

HRID 326664 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6]([C:13]([O:15]C)=O)[NH:7]2.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6]([C:13](=[O:15])[NH:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[NH:7]2

Participants

3

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 14743007Methyl 5,7-dichloro-4-hydroxyquinoline-2-carboxylate

Product 1

HCID 197351845,7-Dichloro-2-[2-(1-pyrrolidinyl) ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline dihydrochloride

Procedure

Treatment of methyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (2 g) with 1(2-aminoethyl-pyrrolidine (10 ml) as described in Example 39 gave 5,7-dichloro-2-[2-(1-pyrrolidinyl) ethyl]carbamoyl-4-oxo-1,4-dihydroquinoline dihydrochloride (1.5 g).,m.p.>280° C. δ (360 MHz, D2O) 2.02 and 2.16 (4H, 2m, pyrrolidinyl-3,4-H), 3.16 (2H, m, CH2N), 3.49 (2H, t, CONHCH2), 3.80 (4H, m, pyrrolidinyl-2,5-H), 6.70 (1H, s, 3-H), 7.43 (1H, d, 6-H) and 7.64 (1H, d, 8-H). (Found: C, 45.02; H, 4.52; N, 9.90%. C16H17Cl2N3O2.2HCl requires C, 44.99; H, 4.48; N, 9.84%).

Sources & evidence

ORD record
ord-d6c30d28decd4ecf832e77f93ec985da
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

Loading…