Sodium Carbonate → 2-Chloro-3-methoxyaniline

HRID 731514노트

반응식

HRID 731514 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

참가 물질

7

반응물 2

HCID 10340Sodium CarbonateHCID 124118272-Chloro-1-methoxy-3-nitrobenzene

생성물 1

HCID 225046772-Chloro-3-methoxyaniline수율 103.5%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

2-Chloro-3-nitroanisole C3 (1.38 g; 7.36 mmol) was dissolved in a mixture of glacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2(3×150 mL). The extracts were combined and washed with saturated brine and then dried over (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline C4 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps. MS 157.9 (MH)+; Homogeneity by HPLC (TFA) @ 220 nm: 86%.

후처리

  1. temperatureat reflux for 3.5 hr
  2. extractionthe product extracted with CH2Cl2(3×150 mL)
  3. washwashed with saturated brine
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c7625b7537e34d1fbd4c84a5f06728e7
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585845B2

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