Ethanol → Ethyl 3-amino-5-bromobenzoate

HRID 2208689ノート

反応式

HRID 2208689 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH4+].[Cl-].[CH2:17](O)C>C(=O)(O)[O-].[Na+].[Fe]>[NH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[CH:11]=1)[C:5]([O:7][CH2:8][CH3:17])=[O:6]

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 239341Methyl 3-bromo-5-nitrobenzoate

生成物 1

HCID 63021768Ethyl 3-amino-5-bromobenzoate収率 99.14%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of methyl 3-bromo-5-nitrobenzoate (17 g, 62.04 mmol) in ethanol (85 mL), was added NH4Cl solution (17 g in 85 mL water, 317.8 mmol) followed by Fe powder (27.82 g, 498.12 mmol). Resulting reaction mass was stirred at 90° C. for 1 h. On completion, reaction mass was filtered and filtrate concentrated till dryness to get solid which was dissolved in sat. sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over sodium sulfate and concentrated to afford the desired compound (15 g, 99.14%).

後処理

  1. customResulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered
  5. concentrationfiltrate concentrated till dryness
  6. customto get solid which
  7. extractionAqueous layer was extracted with ethyl acetate (3×50 mL)
  8. dry with materialCombined organic layers were dried over sodium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-d8a9ca86fb9f485391699a8de7ed255e
出典データセット
uspto-grants-2016_06
特許番号
US09376422B2

反応ノート

読み込み中…