Hexane → HCID 11716135, compound

HRID 735258Notes

Reaction equation

HRID 735258 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:20])[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:19])=[CH:4][C:3]=1[O:21]C.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[OH:21][C:3]1[CH:4]=[C:5]([C:8]2([CH3:20])[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:19])[CH:6]=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 11659391HCID 11659391, compound

Product 1

HCID 11716135HCID 11716135, compoundYield 62.7%

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-hydroxy-3-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (120 mg, 0.40 mmol) and BBr3 (1.60 mL, 1.0 M solution in dichloromethane). After normal workup, the pure objective compound (71 mg, 62%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=3:1): 1H NMR (200 MHz, DMSO-d6) δ 1.57 (s, 3H, CH3), 6.42 (dd, J=8.14, 2.03 Hz, 1H, ArH), 6.59-6.63 (m, 2H, ArH), 7.07 (t, J=7.73 Hz, 2H, ArH), 7.55 (t, J=7.32 Hz, 1H, ArH), 7.68 (d, J=7.32 Hz, 1H, ArH), 9.00 (br s, 1H, OH), 10.93 (br s, 1H, NH); m.p. 259-261° C.; MS(EI) m/e 283 [M+], 268, 255, 237; HRMS m/e cacld. for C16H13N1O4 283.0845, found 283.0849.

Workup

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

Sources & evidence

ORD record
ord-f9ef8678e11a4005a39037f8ce25ecf8
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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