Water → HCID 11407764, compound

HRID 1869818Notes

Reaction equation

HRID 1869818 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](OCC)=O)(=[O:3])[CH3:2].BrC[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:35])[CH:24]=2)[CH:19]=1.O>C(O)C>[C:1]([NH:4][CH:5]([CH2:6][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=3[Cl:34])[CH:24]=2)[CH:19]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14041Acetamidomalonic acid diethyl esterHCID 57987643HCID 57987643, compound

Product 1

HCID 11407764HCID 11407764, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of Na (0.092 g) in ethanol (5 ml) is added diethyl 2-(acetylamino)malonate (0.870 g). The mixture is stirred for 1 h. A solution of 2-(bromomethyl)-6-(2,6-dichlorophenyl)naphthalene 288 (0.978 g) in ethanol (5 ml) is added, under argon. The mixture is stirred under reflux for 5 h. After addition of water (5 ml), the solution is concentrated under vacuum and then diluted with AcOEt (5 ml). The aqueous phase is extracted with AcOEt (3×15 ml). The organic phases are dried over MgSO4, filtrated and evaporated under vacuum. The residue is purified by silica gel chromatography using AcOEt/cyclohexane 20/80 then (40/60) as eluent.

Workup

  1. stirringThe mixture is stirred
  2. temperatureunder reflux for 5 h
  3. concentrationthe solution is concentrated under vacuum
  4. additiondiluted with AcOEt (5 ml)
  5. extractionThe aqueous phase is extracted with AcOEt (3×15 ml)
  6. dry with materialThe organic phases are dried over MgSO4
  7. filtrationfiltrated
  8. customevaporated under vacuum
  9. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-ca591d611c88467792a688a3ae4e9640
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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