Hexane → 5-chloro-3-(4-hydroxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dione

HRID 735266Notes

Reaction equation

HRID 735266 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[C:5]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)([CH3:20])[C:6](=[O:19])[NH:7]2.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[C:5]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)([CH3:20])[C:6](=[O:19])[NH:7]2

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 115606535-chloro-3-(4-methoxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dione

Product 1

HCID 115022065-chloro-3-(4-hydroxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dioneYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 5-chloro-3-(4-methoxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dione (0.03 g, 0.07 mmol) and BBr3(0.22 mL, 1.0 M dichloromethane solution). After normal workup, the pure objective compound (19 mg, 65%) was obtained as slightly yellow solid by recrytalization (n-hexane:EtOAc=1:3): 1H NMR (200 MHz, CDCl3) δ 1.75 (s, 3H, CH3), 2.38 (s, 3H, NCH3), 2.59-2.65 (m, 4H, 2×NCH2), 2.89-2.92 (m, 4H, 2×NCH2), 3.33 (s, 3H, OCH3), 6.52-6.55 (m, 2H, ArH), 6.69-6.74 (m, 2H, ArH), 7.04-7.08 (m, 2H, ArH).

Workup

  1. customThe objective compound was prepared by the same procedure for the example 13

Sources & evidence

ORD record
ord-db56e8c9f6624ab9b888cc2aad61d292
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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