1,3-Dibromopropane → HCID 68574374, compound

HRID 40825Notes

Reaction equation

HRID 40825 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([CH3:20])[CH:14]=[C:13]2[OH:21])=[O:5])[CH3:2].[Br:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([CH3:20])[CH:14]=[C:13]2[O:21][CH2:25][CH2:24][CH2:23][Br:22])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178471686HCID 178471686, compound

Product 1

HCID 68574374HCID 68574374, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reaction between 6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-ol (1.157 g, 4 mmol), 1,3-dibromopropane (3.230 g, 16 mmol) and anhydrous potassium carbonate (0.663 g, 4.8 mmol) in acetone was performed similar to that described in Example 5b. The expected compound was obtained as a white solid (0.903 g, 55%). 1H NMR (400 MHz, CDCl3): 1.25 (3H, t, J=7.2 Hz), 2.18 (2H, m), 2.56 (4H, m), 2.65 (3H, s), 3.67 (2H, t, J=6.3 Hz), 4.14 (4H, m), 4.31 (2H, t, J=5.8 Hz), 6.61 (s, 1H), 7.29 (1H, dd, J=9.1, 2.6 Hz), 7.36 (1H, d, J=2.6 Hz), 7.85 (1H, d, J=9.1 Hz).

Sources & evidence

ORD record
ord-b6752c4b30be4fafa405b0615ad7293e
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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