Hexane → HCID 11680566, compound

HRID 735260Notes

Reaction equation

HRID 735260 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:21])[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:20])=[CH:5][CH:4]=1.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH3:21])[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:20])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 11522001HCID 11522001, compound

Product 1

HCID 11680566HCID 11680566, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (1.00 g, 3.55 mmol) and BBr3 (17.8 mL, 1.0 M solution in dichloromethane). After normal workup, the pure objective compound (0.47 g, 50%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3) δ 1.81 (s, 3H, CH3), 5.20 (br s, 1H, OH), 6.68 (d, J=8.9 Hz, 2H, ArH), 6.85-7.19 (m, 4H, ArH), 7.45-7.89 (m, 2H, ArH), 8.46 (br s, 1H, NH).

Workup

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

Sources & evidence

ORD record
ord-8b51083f540b47ffae654825307a6402
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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