Hydrochloric Acid → HCID 54588554, 화합물

HRID 1467032노트

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HRID 1467032 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([O:22]CC)=[O:21].[OH-].[Na+].Cl>CCO.O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([OH:22])=[O:21]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66746528HCID 66746528, 화합물

생성물 1

HCID 54588554HCID 54588554, 화합물수율 99.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a solution of ethyl 4-amino-5-(cyclohexyloxy)-2-methylquinoline-3-carboxylate (Example 36a, 110 g, 0.335 mol) in EtOH (450 mL) was added a solution of NaOH (33.5 g, 0.837 mol) in water (200 mL) at room temperature. The reaction mixture was then refluxed overnight. The reaction solution was cooled down to 0° C. and carefully neutralized with 4N HCl to pH 7. The resultant solution was concentrated under reduced pressure to remove most of the EtOH. The precipitate was collected by filtration, and re-dissolved in EtOH (4 L) at 65° C. and treated with activated charcoal (5 g) for 0.5 h. The charcoal was removed by filtration over celite, and the filtrate was concentrated. The precipitate was collected by filtration, washed with cold water, and dried under vacuum at 60° C. overnight to give the title compound as a white solid (100 g, 99%). M.p.: 220.0-221.5° C. 1H NMR (400 MHz, DMSO-d6) δ 1.28-1.72 (m, 8H), 2.00-2.04 (m, 2H), 2.75 (s, 3H), 4.69-4.71 (m, 1H), 7.10-7.12 (d, J=8.0 Hz, 1H), 7.24-7.26 (d, J=8.0 Hz, 1H), 7.65 (t, J=8.0 Hz, 1H), 12.80 (brs, 1H). MS 301 (MH+). Elemental Analysis Calculated (Found) for C17H20N2O3: C, 67.98%; (67.74%); H, 6.71%; (7.01%); N, 9.33%; (9.40%).

후처리

  1. temperatureThe reaction mixture was then refluxed overnight
  2. concentrationThe resultant solution was concentrated under reduced pressure
  3. customto remove most of the EtOH
  4. filtrationThe precipitate was collected by filtration
  5. dissolutionre-dissolved in EtOH (4 L) at 65° C.
  6. additiontreated with activated charcoal (5 g) for 0.5 h
  7. customThe charcoal was removed by filtration over celite
  8. concentrationthe filtrate was concentrated
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with cold water
  11. customdried under vacuum at 60° C. overnight

출처 및 근거

ORD 기록
ord-185ebb769fcd4f049aff9c79dd305f20
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000054B2

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