Sodium Carbonate → 2-Chloro-3-methoxyaniline

HRID 731514ノート

反応式

HRID 731514 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

HCID 225046772-Chloro-3-methoxyaniline収率 103.5%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-c7625b7537e34d1fbd4c84a5f06728e7
出典データセット
uspto-grants-2009_09
特許番号
US07585845B2

反応ノート

読み込み中…