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

HRID 2169827ノート

反応式

HRID 2169827 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 166444904-Amino-6-methoxyquinoline-3-carboxylic acid収率 93%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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 1N 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 NR (400 MHz, DMSO-d6) δ 3.89 (s, 3H), 6.40 (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+).

後処理

  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

出典と根拠

ORDレコード
ord-dbeb5459a3684a0e9362bae21f8c17e0
出典データセット
uspto-grants-2015_06
特許番号
US09049878B2

反応ノート

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