Ethanol → Ethyl 3-amino-5-bromobenzoate

HRID 2208689노트

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HRID 2208689 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 63021768Ethyl 3-amino-5-bromobenzoate수율 99.14%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d8a9ca86fb9f485391699a8de7ed255e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376422B2

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