Hydrochloric Acid → HCID 178496276, 화합물

HRID 1805459노트

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HRID 1805459 반응식
[N:1]([O-])=O.[Na+].[F:5][CH:6]([F:15])[O:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].Cl.[CH3:17][O:18][CH2:19][C:20](=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].CC([O-])=O.[Na+]>O.CO>[F:5][CH:6]([F:15])[O:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][N:1]=[C:21]([C:20](=[O:26])[CH2:19][O:18][CH3:17])[C:22]([O:24][CH3:25])=[O:23]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 9346202-(Difluoromethoxy)anilineHCID 23668193Sodium Nitrite

생성물 1

HCID 178496276HCID 178496276, 화합물수율 96%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

A solution of NaNO2 (2.378 g, 34.5 mmol) in H2O (10 mL) was added dropwise at 0° C. to a solution of 2-(difluoromethoxy)aniline (3.59 mL, 28.7 mmol) in 6 M HCl aqueous solution (28.7 mL, 172 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (3.72 mL, 28.7 mmol) and NaOAc (14.14 g, 172 mmol) in MeOH (50 mL) pre-cooled at 0° C. The precipitate was collected by filtration, washed with water, and dissolved in AcOEt. The organic solution was washed with water, saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was washed with hexane/AcOEt (3/1) to give the title compound (8.70 g, 96% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.51 (3H, s), 3.89 (3H×0.5, s), 3.94 (3H×0.5, s), 4.68 (1H×0.5, s), 4.70 (1H×0.5, s), 6.63 (1H×0.5, t, J=72.7 Hz), 6.66 (1H×0.5, t, J=72.3 Hz), 7.10-7.34 (4H, m), 7.67 (1H×0.5, dd, J=8.3, 1.5 Hz), 7.90 (1H×0.5, dd, J=8.3, 1.5 Hz), 13.14 (1H×0.5, s), 14.96 (1H×0.5, br s).

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutiondissolved in AcOEt
  4. washThe organic solution was washed with water, saturated NaHCO3 aqueous solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane/AcOEt (3/1)

출처 및 근거

ORD 기록
ord-21d4b9d1c5964067a963d95a3f89d6ed
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354411B2

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