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

HRID 326659Notes

Reaction equation

HRID 326659 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]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:22])[CH:10]=1)C1C=CC=CC=1.[BrH:33]>C(O)(=O)C>[BrH:33].[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]([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:31])[CH3:32])=[O:22])[NH:12]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 197352282-Diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 197351532-Diisopropylaminoethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Treatment of 2-diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.85 g) with hydrogen bromide in acetic acid (15 ml, 48%) as described in Example 33d gave 2-diisopropylaminoethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide (0.24 g), m.p. 220° C. (dec). δ (360 MHz, DMSO-d6) 1.33 (12H, 2d, CH3), 3.63 (2H, bs, CH2N), 3.74 (2H, m, CH), 4.63 (2H, t, CO2CH2), 6.70 (1H, s, 3-H), 7.46 (1H, d, 6-H), 8.02 (1H, d, 8-H), 8.90 (1H, bs, NH) and 12.14 (1H, bs, NH). (Found: C, 45.44; H, 4.87; N, 5.85%. C18H22Cl2N2O3. HBr.H2O requires C, 45.49; H, 5.09; N, 5.90%).

Sources & evidence

ORD record
ord-2d0a672c97974385bb9295e4e8882de5
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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