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

HRID 1444664노트

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HRID 1444664 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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 ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate (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 1-amino-4-hydroxyquinolin-2(1H)-one 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, 2H) 5.94 (s, 1H) 7.20 (t, J=7.54 Hz, 1H) 7.62 (m, 1H) 7.85 (m, 2H) 11.33 (s, 1H).

후처리

  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

출처 및 근거

ORD 기록
ord-91069141cd1e4da8aae2b9ec128d86ed
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662958B2

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