1-Chloromethylnaphthalene → Diethyl acetamido[(naphthalen-1-yl)methyl]propanedioate

HRID 1457929Notes

Reaction equation

HRID 1457929 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[C:17]1([CH2:27]Cl)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+]>C(O)C.CCCCCC>[C:17]1([CH2:27][C:6]([NH:5][C:2](=[O:4])[CH3:3])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 68451-ChloromethylnaphthaleneHCID 14041Acetamidomalonic acid diethyl esterHCID 516920Potassium bisulfateHCID 5360545Sodium

Product 1

HCID 227964Diethyl acetamido[(naphthalen-1-yl)methyl]propanedioate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium (28 mmol; 0.64 g) is introduced into 50 cm3 of absolute ethanol, under inert atmosphere. At 0° C., diethyl 2-acetamidomalonate (28 mmol; 6.08 g) dissolved in 35 cm3 of absolute ethanol is added, followed by dropwise addition, with a syringe, of (1-naphthyl)methyl chloride (28 mmol; 4.1 cm3). The mixture is maintained at reflux until the starting material has disappeared (6 h, then overnight at room temperature and then 2 h at reflux). The reaction medium is poured onto a KHSO4 (0.05M; 240 cm3)/hexane (120 cm3) mixture and stirred vigorously. A white precipitate, which is the expected malonic derivative, is recovered.

Workup

  1. additionis added
  2. temperatureThe mixture is maintained
  3. temperatureat reflux until the starting material
  4. custom6 h
  5. customis recovered

Sources & evidence

ORD record
ord-73ba73dd8ec349d78eb5d934a8e9043d
Source dataset
uspto-grants-1998_12
Patent number
US05849781

Reaction notes

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