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

HRID 1519749ノート

反応式

HRID 1519749 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, 400MHz): δ13.0 (brs, 1H), 9.65(s, 1H), 8.61(d, 1H, J=4.8Hz), 8.16 (d, 1H, J=4.8Hz), 8.05 (d, 1H, J=6.8Hz), 7.92 (t, 1H), 7.72 (d, 1H, J=6.8Hz), 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-25383730900d4abb859982aee86cf16e
出典データセット
uspto-grants-2015_07
特許番号
US09073891B2

反応ノート

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