Trifluoroacetic acid → 3-Chloro-5-cyanopyridine-2-carboxylic acid

HRID 627686노트

반응식

HRID 627686 반응식
[Cl:1][C:2]1[C:3]([C:10]([O:12]C(C)(C)C)=[O:11])=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 867281412-Pyridinecarboxylic acid, 3-chloro-5-cyano-, 1,1-dimethylethyl ester

생성물 1

HCID 508531763-Chloro-5-cyanopyridine-2-carboxylic acid수율 93.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-chloro-5-cyanopicolinate (1.4 g, 3.23 mmol) in DCM (10.75 ml) was added TFA (25 ml, 323 mmol). The orange solution was stirred at RT for 1 hr. It was concentrated. Then the residue was passed through a PEAX column and the acid was eluted with 2% conc. HCl in MeOH (0.3 mL in 15 mL MeOH) to yield 3-chloro-5-cyanopicolinic acid (0.55 g, 3.01 mmol, 93% yield) as yellow solid. MS m/z=183 (M+H).

후처리

  1. concentrationIt was concentrated
  2. washthe acid was eluted with 2% conc. HCl in MeOH (0.3 mL in 15 mL MeOH)

출처 및 근거

ORD 기록
ord-e05e5fea18cc4b31880d716dc83428dd
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

반응 노트

불러오는 중…