Ammonia → 2-(Isoquinolin-8-YL)acetic acid

HRID 2097961노트

반응식

HRID 2097961 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH:4]=[CH:3][N:2]=1.C(O)(C(F)(F)F)=O.N>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([OH:14])=[O:13])[CH:4]=[CH:3][N:2]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 68757728Tert-butyl 2-(isoquinolin-8-yl)acetate

생성물 1

HCID 179072422-(Isoquinolin-8-YL)acetic acid수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 2-(isoquinolin-8-yl)acetate (1.8 g) in DCM (10 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction was complete, the solvent was removed to give a residue which was adjusted to pH 3-4 with aqueous ammonia. The precipitate was filtered off and washed with water. The final product was purified (silica gel coulumn chromatography) to afford 2-(isoquinolin-8-yl)acetic acid as a solid (1.2 g, 87%). LC-MS (0.05% TFA): [M+1]+ 188.1. 1H-NMR (DMSO-d6, 400 MHz): 613.0 (brs, 1H), 9.65 (s, 1H), 8.61 (d, 1H, J=4.8 Hz), 8.16 (d, 1H, J=4.8 Hz), 8.05 (d, 1H, J=6.8 Hz), 7.92 (t, 1H), 7.72 (d, 1H, J=6.8 Hz), 4.29 (s, 2H).

후처리

  1. customthe solvent was removed
  2. customto give a residue which
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe final product was purified (silica gel coulumn chromatography)

출처 및 근거

ORD 기록
ord-b7509202bf81436aaa4623f58b6f1cc4
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450363B2

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