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

HRID 326653Notes

Reaction equation

HRID 326653 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]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:22])[CH:10]=1)C1C=CC=CC=1.[BrH:31].CCOCC>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]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:22])[NH:12]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 197351892-Diethylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 197351512-Diethylaminoethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-diethylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.55 g) at room temperature was added hydrogen bromide in acetic acid (15 ml of a 48% solution) and the solution was stirred in a sealed flask for 48 hours. The reaction mixture was poured into dry ether (50 ml) to give a pale yellow solid which was filtered off and recrystallised from ethanol to yield 2-diethylaminoethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide (0.36 g), m.p. 220° C. (dec). δ (360 MHz, DMSO-d6), 1.25 (6H, t, CH3), 3.28 (4H, m, NCH2CH3), 3.57 (2H, m, OCH2CH2N), 4.66 (2H, t, OCH2CH2), 6.86 (1H, s, 3-H), 7.47 (1H, d, 6-H), 8.05 (1H, d, 8-H), 9.37 (1H, bs, NH) and 12.1 (1H, vbs, NH). (Found: C, 40.20; H, 4.15; N, 5.86%. C16H18Cl2N2O3. 1.5HBr requires C, 40.15; H, 4.10; N, 5.85%).

Workup

  1. customto give a pale yellow solid which
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-8e5159d970ee43bc920e9e30fd122ce0
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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