Hydrogen Bromide → 2-(1-Pyrrolidinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

HRID 326655Notes

Reaction equation

HRID 326655 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[N:12]=[C:11]([C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:22])[CH:10]=1)C1C=CC=CC=1.[BrH:31]>C(O)(=O)C>[BrH:31].[Cl:19][C:17]1[CH:16]=[C:15]([Cl:20])[CH:14]=[C:13]2[C:18]=1[C:9](=[O:8])[CH:10]=[C:11]([C:21]([O:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:22])[NH:12]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 197351692-(1-Pyrrolidinyl)ethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 197351642-(1-Pyrrolidinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Treatment of 2-(1-pyrrolidinyl)ethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.65 g) with hydrogen bromide in acetic acid (5 ml, 48%) as described in Example 33d gave 2-(1-pyrrolidinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide (0.3 g), m.p. 258° C. (dec). δ (250 MHz, DMSO-d6) 2.04 (4H, m, pyrrolidine-3,4-H), 3.18 (2H, m, CH2N) 3.68 (4H, m, pyrrolidine-2.5-H), 4.68 (2H, t, CO2CH2), 6.91 (1H, s, 3-H), 7.46 (1H, d, 6-H), 8.08 (1H, d, 8-H), 9.90 (2H, vbs, NH). (Found: C, 41.24; H, 3.68; N, 6.03%. C16H16Cl2N2O3. 1.35HBr requires C, 41.38; H, 3.76; N, 6.03%).

Sources & evidence

ORD record
ord-a5d352ff00c24dce88e908f13ed815cd
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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