Methyl 2-amino-3-hydroxy-5-methylbenzoate → Methyl 2-amino-6-methylbenzoxazole-4-carboxylate

HRID 249921

Reaktionsgleichung

Reaktionsgleichung von HRID 249921
[N:1]1(C(N2C=CN=C2)N)C=CN=[CH:2]1.[NH2:13][C:14]1[C:23]([OH:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>C1COCC1>[NH2:1][C:2]1[O:24][C:23]2[C:14](=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:20]=[C:21]([CH3:25])[CH:22]=2)[N:13]=1

Komponenten

4

Edukt 2

HCID 21755136Methyl 2-amino-3-hydroxy-5-methylbenzoateHCID 66874404di(1H-imidazole-1-yl)methanamine

Produkt 1

HCID 66874433Methyl 2-amino-6-methylbenzoxazole-4-carboxylateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of di (1H-imidazole-1-yl)methanamine (1.56 g, 9.67 mmol) in THF (30 mL) was added methyl 2-amino-3-hydroxy-5-methylbenzoate (1.40 g, 7.73 mmol) at room temperature and the resulting reaction mixture was heated at reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), treated with saturated aqueous ammonium chloride (25 mL), and then extracted with CH2Cl2 (2×100 mL). The combined organic phase was washed with brine (2×100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford a yellow solid. The solid was triturated from CH3OH to afford methyl 2-amino-6-methylbenzoxazole-4-carboxylate (0.717 g, 45%). 1H NMR and MS consistent.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 6 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  6. additiontreated with saturated aqueous ammonium chloride (25 mL)
  7. extractionextracted with CH2Cl2 (2×100 mL)
  8. washThe combined organic phase was washed with brine (2×100 mL)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto afford a yellow solid
  13. customThe solid was triturated from CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-1e57ef9aef8b42c0acadced7b7b9d7e4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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