Ethanol → Ethyl 3-amino-5-bromobenzoate

HRID 2208689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208689
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 63021768Ethyl 3-amino-5-bromobenzoateAusbeute 99,14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d8a9ca86fb9f485391699a8de7ed255e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376422B2

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