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Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

HRID 384790
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HRID 384790 반응식
[CH3:1][O:2][C:3]1[C:4]([O:16][CH2:17][CH2:18][Cl:19])=[CH:5][C:6]([N+:13]([O-])=O)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[H][H]>[Pt]=S.[C].CO>[CH3:1][O:2][C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]([NH2:13])=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][Cl:19]
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참가 물질

5

반응물 2

HCID 23032998Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 23033001Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate수율 101.6%

시약·촉매·용매 2

HCID 178505369HCID 178505369, 화합물촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet were placed 1.02 g (3.45 mmol) of methyl 5-methoxy-4-(2-chloroethoxy)-2-nitrobenzoate (purity: 98%) obtained in Reference Example III-2 and 20 mL of methanol. The resulting mixture was heated to 50° C. under stirring. To the mixture was added 0.5 g of 3 wt. % platinum sulfide/carbon (containing 65.7% water) at the same temperature. The resulting mixture was heated to the same temperature for one hour, while hydrogen was introduced to the mixture under atmospheric pressure at a rate of 50 mL/min. After the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure, to precipitate a crystalline product. The crystalline product was dried under reduced pressure, to give 0.91 g (isolated yield: 93.0%, purity: 99% in terms of area percentage determined by high performance liquid chromatography) of methyl 5-methoxy-4-(2-chloroethoxy)-anthranilate as a white crystalline product.

후처리

  1. customIn a 50 mL volume glass flask equipped with a stirrer
  2. additionwas introduced to the mixture under atmospheric pressure at a rate of 50 mL/min
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto precipitate a crystalline product
  6. customThe crystalline product was dried under reduced pressure

출처 및 근거

ORD 기록
ord-e3ae948c013b4cef846c166c4518d8e0
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367824B2

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