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

HRID 2097961ノート

反応式

HRID 2097961 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 179072422-(Isoquinolin-8-YL)acetic acid収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b7509202bf81436aaa4623f58b6f1cc4
出典データセット
uspto-grants-2013_05
特許番号
US08450363B2

反応ノート

読み込み中…