Acetic Acid → 6-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

HRID 594260노트

반응식

HRID 594260 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][N:3]=1.[CH2:12]1N2CN3CN(C2)CN1C3.Cl.[C:23](O)(=[O:25])C>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[C:10]=1[CH:23]=[O:25]

참가 물질

5

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 1354978903-Methyl-1,2-benzisoxazol-6-ol

생성물 1

HCID 824037016-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

실험 절차

To a solution of commercially available 3-methylbenzo[d]isoxazol-6-ol (1.125 g; 7.54 mmol) in acetic acid (22.5 ml) was added hexamethylenetetramine (4.500 g; 32.09 mmol), and the resulting mixture was heated over a steam-bath for 6 h. The resulting hot mixture was then treated with 6 M aq. HCl (20 ml), and the heating was continued for 30 min. The solid obtained on dilution of the reaction mixture was filtered, and recrystallised from aq. MeOH to give the desired 6-hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde as a yellow solid. LC-MS (conditions D): tR=0.79 min.; [M+H]+: 177.98 g/mol.

후처리

  1. temperaturethe resulting mixture was heated over a steam-bath for 6 h
  2. customThe solid obtained on dilution of the reaction mixture
  3. filtrationwas filtered
  4. customrecrystallised from aq. MeOH

출처 및 근거

ORD 기록
ord-93cb3a49d9f74287ad5b715d5936c208
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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