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

HRID 249921

반응식

HRID 249921 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e57ef9aef8b42c0acadced7b7b9d7e4
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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