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

HRID 735248Notes

Reaction equation

HRID 735248 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH3:29])[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([Cl:27])=[CH:21][C:22]=3[Cl:26])[NH:17][C:16]2=[O:28])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2([CH3:29])[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([Cl:27])=[CH:21][C:22]=3[Cl:26])[NH:17][C:16]2=[O:28])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 115754793-(3-benzyloxy-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 115590903-(3-hydroxy-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 3-(3-benzyloxy-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.26 g, 0.60 mmol) and BBr3 (1.20 mL, 1.0 M dichloromethane solution). After normal workup, the objective compound (0.18 g, 90%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3+DMSO-d6) δ 1.62 (s, 3H, CH3), 6.57-6.71 (m, 3H, ArH), 6.98-7.12 (m, 3H, ArH), 9.17 (s, 1H, OH), 11.07 (s, 1H, NH); m.p. 248° C. (decomp.); MS(EI) m/e 335 [M+], 148, 91.

Workup

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

Sources & evidence

ORD record
ord-dd5e178195c449bdb07948bd5e1c6d2f
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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