Hydrogen Bromide → 3-Dimethylaminopropyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

HRID 326657Notes

Reaction equation

HRID 326657 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][CH2:26][N:27]([CH3:29])[CH3:28])=[O:22])[CH:10]=1)C1C=CC=CC=1.[BrH:30]>C(O)(=O)C>[BrH:30].[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][CH2:26][N:27]([CH3:29])[CH3:28])=[O:22])[NH:12]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 197351613-Dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 197351863-Dimethylaminopropyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Treatment of 3-dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.52 g) with hydrogen bromide in acetic acid (10 ml, 48%) as described in Example 33d gave 3-dimethylaminopropyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide (0.27 g), m.p. 228° C. (dec). δ (360 MHz, DMSO-d6) 2.13 (2H, m, CO2CH2CH2), 2.81 (6H, s, (CH3)2) 3.25 (2H, t, CH2N), 4.42 (2H, t, CO2CH2), 6.72 (1H, s, 3-H), 7.45 (1H, d, 6-H), 8.01 (1H, d, 8-H), 9.43 (1H, bs, NH) and 12.04 (1H, bs, NH). (Found: C, 41.60; H, 4.34; N, 6.04%. C15H16Cl2N2O2. HBr.0.4H2O requires C, 41.77; H, 4.16; N, 6.49%).

Sources & evidence

ORD record
ord-8958b490ae3846c59422d1906f1e05d3
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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