Anthranilic acid, 3-hydroxy-, methyl ester → Methyl 2-amino-1,3-benzoxazole-4-carboxylate

HRID 249843

Reaktionsgleichung

Reaktionsgleichung von HRID 249843
[N:1]1(C(N2C=CN=C2)N)C=CN=[CH:2]1.[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]=1[NH2:23]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[O:22][C:18]2[C:17](=[C:16]([C:15]([O:14][CH3:13])=[O:24])[CH:21]=[CH:20][CH:19]=2)[N:23]=1

Komponenten

5

Edukt 2

HCID 205248Anthranilic acid, 3-hydroxy-, methyl esterHCID 66874404di(1H-imidazole-1-yl)methanamine

Produkt 1

HCID 66873567Methyl 2-amino-1,3-benzoxazole-4-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of di(1H-imidazole-1-yl)methanamine (2.05 g, 12.26 mmol) in THF (60 mL) was added methyl-2-amino-3-hydroxybenzoate (1.98 g, 12.26 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 17 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL) and washed with H2O (3×100 mL), saturated ammonium chloride (2×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by recrystallization from diethyl ether to afford methyl 2-aminobenzoxazole-4-carboxylate (1.10 g, 50%) as a brown solid. 1H NMR and MS consistent.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 17 h
  4. washwashed with H2O (3×100 mL), saturated ammonium chloride (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by recrystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0ed8eab141044d9a93ad410e4d2895c7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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