Sodium Hydroxide → 4-Amino-6-methoxyquinoline-3-carboxylic acid

HRID 1466969노트

반응식

HRID 1466969 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=[O:15].[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 16644472Ethyl 4-amino-6-methoxyquinoline-3-carboxylate

생성물 1

HCID 166444904-Amino-6-methoxyquinoline-3-carboxylic acid수율 93%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of ethyl 4-amino-6-methoxyquinoline-3-carboxylate (Example 1a, 1.23 g, 5.0 mmol) in EtOH (20.0 mL) was added aqueous NaOH (2.0 N, 5.0 mL) at room temperature. The reaction mixture was then refluxed for 3 hr. The solution was then filtered and washed with water. The filtrate was cooled to 0° C. and neutralized carefully with 1 N HCl to pH 7. Most of the EtOH was removed under reduced pressure, and the precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as an off-white solid (1.01 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 3.89 (s, 3H), 7.40 (dd, J=2.8, 9.4 Hz, 1H), 7.73 (d, J=9.4 Hz, 1H), 7.77 (d, J=2.8 Hz, 1H), 8.77 (s, 1H). MS 219 (MH+).

후처리

  1. temperatureThe reaction mixture was then refluxed for 3 hr
  2. filtrationThe solution was then filtered
  3. washwashed with water
  4. customMost of the EtOH was removed under reduced pressure
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with cold water
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-762e5f6f12a7435bb9d34702e1bfd3f4
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000054B2

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