Sulfuric Acid → 3-Amino-6-(trifluoromethyl)picolinamide

반응식

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[N:6][C:7]=1[C:8]#[N:9].S(=O)(=O)(O)[OH:15]>>[NH2:1][C:2]1[C:7]([C:8]([NH2:9])=[O:15])=[N:6][C:5]([C:10]([F:13])([F:11])[F:12])=[CH:4][CH:3]=1

참가 물질

반응물 2

HCID 1118Sulfuric Acid

HCID 573645173-Amino-6-(trifluoromethyl)picolinonitrile

생성물 1

HCID 578899673-Amino-6-(trifluoromethyl)picolinamide

반응 조건

온도: 70 °C

실험 절차

7 g (0.0374 mol, 1 eq) of 5-amino-6-cyano-2-(trifluoromethyl)pyridine dissolved in 106 ml of 90% sulfuric acid was and heated at 70° C. for 3 h. The reaction mixture was cooled to RT and quenched with ice water and extracted with ethyl acetate. The organic layer was washed with brine and concentrated. The solid product obtained was washed with to get 6.8 g (89.47%) of off white solid. 1H NMR (CDCl3, 400 MHz) 5.5 (1H, bs), 7.1 (1H, d), 7.53 (1H, d), 7.80 (1H, bs). MS 206 (M+H)+.

후처리

temperatureThe reaction mixture was cooled to RT
customquenched with ice water
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
concentrationconcentrated
customThe solid product obtained
washwas washed with
customto get 6.8 g (89.47%) of off white solid

출처 및 근거

ORD 기록: ord-4c7721ac1a434048991f19fb8b60b865
출처 데이터셋: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07601844B2

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