Dichloromethane → Ethyl 3-(isopropylamino)benzoate

HRID 400529

Reaktionsgleichung

Reaktionsgleichung von HRID 400529
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH:21]([NH2:24])([CH3:23])[CH3:22].ClCCl>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:21]([NH:24][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:23])[CH3:22]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 6363IsopropylamineHCID 62657Potassium Phosphate, TribasicHCID 90488Ethyl 3-bromobenzoate

Produkt 1

HCID 43087836Ethyl 3-(isopropylamino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Potassium phosphate (1.38 g, 6.5 mmol), palladium(II) acetate (56 mg, 0.25 mmol), and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine (139 mg, 0.25 mmol) were combined in a microwave tube under nitrogen. Ethyl 3-bromobenzoate (1.145 g, 5 mmol) in dimethoxyethane (2 mL) and isopropylamine (385 mg, 6.5 mmol) in dimethoxyethane (2 mL) were added. The tube was filled with nitrogen again. The tube was then capped, and the reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts) with stirring at 160° C. for 70 minutes. Then dichloromethane was added, and the crude mixture was filtered. The filtrate was concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1) to give ethyl 3-(isopropylamino)benzoate.

Aufarbeitung

  1. additionThe tube was filled with nitrogen again
  2. customThe tube was then capped
  3. temperaturethe reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts)
  4. filtrationthe crude mixture was filtered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-298c13724bb8494f8703f9520bb511b1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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