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

HRID 735247Notes

Reaction equation

HRID 735247 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:30])[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[CH2:23]([O:22][C:18]1[CH:17]=[C:16]([C:14]2([CH3:15])[C:3](=[O:2])[C:4]3[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][C:9]=3[Cl:10])[NH:12][C:13]2=[O:30])[CH:21]=[CH:20][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 688162202-[2-(3-Benzyloxy-phenyl)-propionylamino]-4,6-dichloro-benzoic acid methyl ester

Product 1

HCID 115754793-(3-benzyloxy-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 4,6-dichloro-2-[2-(3-benzyloxy-phenyl)-propionylamino]-benzoic acid methyl ester (2.80 g, 6.40 mmol) and LiHMDS (19.0 mmol, 1M THF solution). After normal workup, the objective compound (1.90 g, 71%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=9:1): 1H NMR (200 MHz, DMSO-d6) δ 1.55 (s, 3H, CH3), 5.02 (s, 2H, OCH2), 6.69-7.02 (m, 2H, ArH), 7.22-7.38 (m, 7H, ArH), 11.28 (br s, 1H, NH); m.p. 201-203° C.; MS(EI) m/e 426 [M++1], 160, 91.

Workup

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

Sources & evidence

ORD record
ord-4a2cbb450a7b43f2b2fc6c9a495f4eab
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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