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

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.

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

ORDレコード

ord-1e57ef9aef8b42c0acadced7b7b9d7e4

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07863271B2