Lithium Hydroxide → 3-(Methyl(phenyl)amino)-3-oxopropanoic acid

HRID 418594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418594
Cl[C:2](=[O:8])[CH2:3][C:4]([O:6]C)=[O:5].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Li+].[OH-]>C(Cl)Cl.O>[CH3:9][N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2](=[O:8])[CH2:3][C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 3

HCID 3939Lithium HydroxideHCID 7515N-MethylanilineHCID 123460Methyl malonyl chloride

Produkt 1

HCID 3500563-(Methyl(phenyl)amino)-3-oxopropanoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 3-chloro-3-oxopropanoate (1 mL, 9.32 mmol) and N-methyl aniline (1.01 mL, 9.32 mmol) in DCM (18.6 mL) was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue (N-methyl-N-phenyl-malonamic acid methyl ester, 2.55 g) was dissolved in THF (9 mL). A solution of LiOH×H2O (0.782 g, 18.64 mmol) in water (9 mL) was added and the mixture stirred for 1 h at room temperature. The THF was removed under reduced pressure and the remaining aqueous solution was acidified with 1N HCl (until pH-3) then extracted with EtOAc. The organic phase was concentrated under reduced pressure to afford the acid 31 (1.67 g, 93% yield) as a brown foam. MS (m/z): 194.0 (M+H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue (N-methyl-N-phenyl-malonamic acid methyl ester, 2.55 g) was dissolved in THF (9 mL)
  3. customThe THF was removed under reduced pressure
  4. extractionthen extracted with EtOAc
  5. concentrationThe organic phase was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-554b8cb1bf9f44818c74dcf4318dad2f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093264B2

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