Trimethyl orthoformate → 1,3-Benzoxazole-7-carboxylic acid

반응식

[NH2:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:12](OC)(OC)OC>>[O:11]1[C:3]2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=[CH:12]1

참가 물질

반응물 2

HCID 9005Trimethyl orthoformate

HCID 684433-Aminosalicylic acid

생성물 1

HCID 183553101,3-Benzoxazole-7-carboxylic acid

실험 절차

A solution of 3-amino-2-hydroxy-benzoic acid (12.5 mmol) in trimethyl orthoformate (19.2 mL) is heated to reflux for 20 h and concentrated in vacuo. The residue is washed three times with hot MeOH, the filtrates are combined and the solvent is removed in vacuo to give the desired product which is used without further purification. 1H-NMR (DMSO-d6): δ=13.4 (bs, 1H); 8.87 (s, 1H); 8.08 (d, J=8.0 Hz, 1H); 7.96 (d, J=7.5 Hz, 1H); 7.52 (t, J=7.9 Hz, 1H).

후처리

temperatureto reflux for 20 h
concentrationconcentrated in vacuo
washThe residue is washed three times with hot MeOH
customthe solvent is removed in vacuo

출처 및 근거

ORD 기록: ord-eb43d318344b4462a94fa34419a801f6
출처 데이터셋: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08063099B2

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