Potassium Iodide → Methyl 6-bromo-3-[(2-ethoxycarbonyl)propan-2-yl]amino-2-nitrobenzoate

HRID 215807노트

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HRID 215807 반응식
[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([C:9]([Br:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[C:17]([CH3:24])(C)[C:18]([O:20][CH2:21][CH3:22])=[O:19].[I-].[K+].[C:27](=O)([O-])[O-].[Cs+].[Cs+]>O.C(OCC)(=O)C>[Br:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([N+:13]([O-:15])=[O:14])[C:2]([NH:1][CH:24]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:27])=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 58891824Methyl 3-amino-6-bromo-2-nitrobenzoate

생성물 1

HCID 67210813Methyl 6-bromo-3-[(2-ethoxycarbonyl)propan-2-yl]amino-2-nitrobenzoate수율 31%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of methyl 3-amino-6-bromo-2-nitrobenzoate (Reference Compound No. 1-(4), 11.6 g, 42.0 mmol), ethyl 2-bromoisobutyrate (60.4 mL, 412 mmol), potassium iodide (7.76 g, 46.2 mmol) and cesium carbonate (56.1 g, 172 mmol) was stirred at 85° C. for 4 days. After cooling down, ethyl acetate (500 mL) and water (500 mL) were added thereto, the mixture was partitioned, and then the water layer was extracted with ethyl acetate (300 mL). The organic layer was combined, washed with water (1 L, twice) and saturated brine (1 L) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (5.08 g) as an orange oil. (Yield 31%)

후처리

  1. temperatureAfter cooling down
  2. customthe mixture was partitioned
  3. extractionthe water layer was extracted with ethyl acetate (300 mL)
  4. washwashed with water (1 L
  5. dry with materialtwice) and saturated brine (1 L) successively, dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-751e899bc38d44f7802766a0ce26b50e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193187B2

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