Nitric Acid → 2,5-Dimethyl-1H-imidazole-4-carbaldehyde

반응식

[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[C:5]([CH2:7][OH:8])[N:6]=1.[N+]([O-])(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[C:5]([CH:7]=[O:8])[N:6]=1

참가 물질

반응물 3

HCID 944Nitric Acid

HCID 10340Sodium Carbonate

HCID 12647302HCID 12647302, 화합물

생성물 1

HCID 132064322,5-Dimethyl-1H-imidazole-4-carbaldehyde

실험 절차

A 42.2 gm. portion of 2,5-dimethyl-4-imidazolemethanol and 44.8 ml. of concentrated nitric acid are mixed. When the initial reaction subsides, the solution is heated on a steam bath for one hour. The reaction mixture is neutralized with concentrated aqueous sodium carbonate, then concentrated under vacuum. After leaching the residue with 150 ml. of hot ethanol several times, the combined organic solutions are concentrated under vacuum. Chromatographing the residual oil on silica gel gives a solid which is recrystallized from 2-propanol-ethyl acetate to give the desired product, m.p. 164.5°-166° C.

후처리

customWhen the initial reaction subsides
temperaturethe solution is heated on a steam bath for one hour
concentrationconcentrated under vacuum
concentrationof hot ethanol several times, the combined organic solutions are concentrated under vacuum
customChromatographing the residual oil on silica gel gives a solid which
customis recrystallized from 2-propanol-ethyl acetate

출처 및 근거

ORD 기록: ord-5b940e22f28a4bd08d27dcd81b06e1c0
출처 데이터셋: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04107308

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