Potassium Hydroxide → 1-amino-4-hydroxyquinolin-2(1H)-one

HRID 601327ノート

反応式

HRID 601327 の反応式
[OH-].[K+].[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([N:14]=CC2C=CC=CC=2)[C:6](=[O:22])[C:5]=1C(OCC)=O>O1CCOCC1>[NH2:14][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([OH:3])=[CH:5][C:6]1=[O:22]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 67063863Ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate

生成物 1

HCID 591688071-amino-4-hydroxyquinolin-2(1H)-one収率 91%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 25% by weight aqueous potassium hydroxide (200 mL) and 1,4-dioxane (50 mL) heated to 90-100° C. was added portion wise the product of Example 226C (6.72 g, 20.0 mmol). The reaction mixture was heated at reflux for 90 minutes allowing distillation to occur and additional water and dioxane (30 mL each) were added to the reaction vessel to reach the original volume. The mixture was refluxed for an additional 90 minutes with distillation, cooled, washed with 200 mL of 1:1 diethyl ether/ethyl acetate, acidified with concentrated hydrochloric acid to pH 2 and the resulting solid was collected by filtration, washed with water and dried to constant mass to give the title compound as a tan sold (3.22 g, 91% yield). MS (DCI) m/z 177 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 5.56 (s, 2 H) 5.94 (s, 1 H) 7.20 (t, J=7.54 Hz, 1 H) 7.62 (m, 1 H) 7.85 (m, 2 H) 11.33 (s, 1 H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 90 minutes
  3. distillationdistillation
  4. additionadditional water and dioxane (30 mL each) were added to the reaction vessel
  5. temperatureThe mixture was refluxed for an additional 90 minutes with distillation
  6. temperaturecooled
  7. washwashed with 200 mL of 1:1 diethyl ether/ethyl acetate
  8. filtrationthe resulting solid was collected by filtration
  9. washwashed with water
  10. customdried to constant mass

出典と根拠

ORDレコード
ord-93d3ed1968f84efda30c3023bec94e12
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

反応ノート

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