Hydrogen Bromide → 2-Dimethylamino-1-methylethyl 5,7-dichloroquinoline-2-carboxylate hydrobromide

HRID 326661Notes

Reaction equation

HRID 326661 reaction equation
C(O[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][CH:24]([CH3:29])[CH2:25][N:26]([CH3:28])[CH3:27])=[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[CH:9]=[CH:10][C:11]([C:21]([O:23][CH:24]([CH3:29])[CH2:25][N:26]([CH3:28])[CH3:27])=[O:22])=[N:12]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 536755692-Dimethylamino-1-methylethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 678548702-Dimethylamino-1-methylethyl 5,7-dichloroquinoline-2-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Treatment of 2-dimethylamino-1-methylethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (1.4 g) with hydrogen bromide in acetic acid (15 ml, 48%) as described in Example 33d gave 2-dimethylamino-1-methylethyl 5,7-dichloroquinoline-2-carboxylate hydrobromide (0.32 g), m.p. 228° C. (dec). δ (360 MHz, DMSO-d6) 1.37 (3H, d, CHCH3), 2.86 (6H, s, N(CH3)2), 3.59 (2H, m, CH2N), 5.47 (1H, m, CO2CH), 6.81 (1H, s, 3-H), 7.45 (1H, d, 6-H), 8.05 (1H, d, 8-H), 9.45 (1H, bs, NH) and 12.02 (1H, bs, NH). (Found: C, 39.67; H, 3.93; N, 5.94%. C15H16Cl2N2O3. 1.4HBr requires C, 39.47; H, 3.84; N, 6.14 %).

Sources & evidence

ORD record
ord-2dd8dcc2d57040a6b79d4c48784438d4
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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