Sodium Hydroxide → 2-(Isoquinolin-5-YL)acetic acid

HRID 353925

반응식

HRID 353925 반응식
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2.[OH-].[Na+]>C(O)(=O)C>[CH:10]1[C:11]2[C:6](=[C:5]([CH2:4][C:3]([OH:15])=[O:2])[CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 22337565Methyl 2-(isoquinolin-5-yl)acetate

생성물 1

HCID 120187082-(Isoquinolin-5-YL)acetic acid수율 47%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
50 °C

실험 절차

Isoquinolin-5-yl-acetic acid methyl ester (Preparation 6, Step 3; 90 mg, 0.448 mmol) was treated with aqueous sodium hydroxide (4N, 3 mL) and the solution was heated at 50° C. for 4 h. The solution was cooled to 0° C. and acetic acid (2 mL) was added dropwise, which resulted in the formation of a precipitate. The mixture was kept at 0° C. overnight (ca. 15 h) and the precipitate was removed via filtration and was washed with water. The solid was dried in air to afford 35 mg (47% yield) of isoquinolin-5-yl-acetic acid; 1H NMR (400 MHz, CD3OD) δ9.24 (s, 1H), 8.47 (d, J=6.2 Hz, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.96 (d, J=6.2 Hz, 1H), 7.74 (d, J=6.6 Hz, 1H), 7.66 (t, J=7.6 Hz, 1H), 4.11 (s, 2H); MS (AP/Cl): 188.3 (M+H)+.

후처리

  1. temperatureThe solution was cooled to 0° C.
  2. customwhich resulted in the formation of a precipitate
  3. custom(ca. 15 h) and the precipitate was removed via filtration
  4. washwas washed with water
  5. customThe solid was dried in air

출처 및 근거

ORD 기록
ord-2ac3caef68e540c7b5e7e4afe23831e2
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756385B2

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