Chloroacetyl chloride → Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

HRID 560271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560271
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[OH:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:6][O:7][C:8]([C:9]1[C:10]2[O:16][CH2:2][C:3](=[O:4])[NH:15][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:17]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Produkt 1

HCID 23770643Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

At RT chloro-acetyl chloride (29.0 mmol) is added dropwise to a solution of 3-amino-2-hydroxy-benzoic acid methyl ester (26.4 mmol) in DMF (100 mL). After 20 min K2CO3 (126 mmol) is added portionwise, the mixture is stirred for 16 h at RT and the solvents are removed in vacuo. Water and DCM are added, the layers are separated and the organic layer is washed with brine and dried over Na2SO4. The solvents are removed in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.68 min; [M+H]+=208.0.

Aufarbeitung

  1. customthe solvents are removed in vacuo
  2. additionWater and DCM are added
  3. customthe layers are separated
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvents are removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84b07eefd193462383f41501944ee39c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063099B2

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