Acetic Acid → 5-Hydroxybenzo[d]oxazole-4-carbaldehyde

반응식

ClC1C=C[C:9]2[C:8]([CH:12]=[O:13])=[C:7]([OH:14])[CH:6]=[CH:5][C:4]=2N=1.C1N2CN3[CH2:24][N:18](C2)CN1C3.CC(O)=[O:27]>>[OH:14][C:7]1[C:8]([CH:12]=[O:13])=[C:9]2[N:18]=[CH:24][O:27][C:4]2=[CH:5][CH:6]=1

참가 물질

반응물 3

HCID 176Acetic Acid

HCID 4101Hexamethylenetetramine

HCID 866834282-Chloro-6-hydroxyquinoline-5-carbaldehyde

생성물 1

HCID 874070885-Hydroxybenzo[d]oxazole-4-carbaldehyde수율 25%

반응 조건

온도: 90 °C

실험 절차

A mixture of compound 3 (350 mg, 1.05 mmol) and HMTA (560 mg, 4 mmol) in AcOH (35 mL) was heated to 90° C. under N2 for 1.5 h. The reaction was monitored by LCMS. After cooled to RT, the solvent was removed under vacuum. The residue was purified by prep-HPLC to give 5-hydroxybenzo[d]oxazole-4-carbaldehyde (152 mg, 25% yield). 1HNMR (DMSO, 400 MHz): δ 10.99 (s, 1H, OH), 10.53 (s, 1H, CHO), 8.86 (s, 1H, ArH), 8.00 (d, 1H, J=9.2 Hz, ArH), 7.05 (d, 1H, J=8.8 Hz, ArH). MS [ESI, MH+]: 164.1.