Hydrochloric Acid → Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

HRID 508831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508831
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH:14]=[N:15]O)=[CH:4][CH:3]=1.Cl>CO.[Zn]>[NH2:15][CH2:14][C:5]1[C:6]([F:13])=[C:7]([C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 76800184Ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

Produkt 1

HCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoateAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate (0.800 g, 3.26 mmol) in MeOH (5 mL) was added Zn (0.850 g, 13.06 mmol), followed by dropwise addition of conc. HCl (catalytic) and the reaction mixture was heated at 60° C. for 2-3 h. Excess of solvent was removed under vacuum and the residue was diluted with water and basified with NaHCO3, extracted with EtOAc and concentrated to afford 0.600 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, J=7.2 Hz, 3H), 3.76 (s, 2H), 4.38 (q, J=6.9 Hz, 2H), 7.41 (d, J=8.1 Hz, 1H), 7.65 (t, J=8.1 Hz, 1H).

Aufarbeitung

  1. customExcess of solvent was removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-021ec19d312e4e1f9b4eb7039ee5d178
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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