Hydrochloric Acid → 2-Amino-3-(benzyloxy)-6-methoxybenzamide

HRID 922402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922402
[CH2:1]([O:8][C:9]1[C:10]([N+:20]([O-])=O)=[C:11]([C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:12]([NH2:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>CCO.[Fe]>[NH2:20][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=[C:15]([O:18][CH3:19])[C:11]=1[C:12]([NH2:14])=[O:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 867193593-(Benzyloxy)-6-methoxy-2-nitrobenzamide

Produkt 1

HCID 867193602-Amino-3-(benzyloxy)-6-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-(benzyloxy)-6-methoxy-2-nitrobenzamide (10, 0.34 g. 1.1 mmol), iron powder (0.44 g, 7.7 mmol) and concentrated hydrochloric acid (80 mL) in EtOH (4 mL)/water (0.4 mL) was heated at 90° C. for 75 min. The reaction mixture was cooled to room temperature, filtered through Celite and concentrated. The residue was dissolved in EtOAc washed with saturated NaHCO3 solution, dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography eluting with 0-10% MeOH in CH2Cl2 afforded the title compound along with its regioisomer (0.267 g, 87%) as a tan solid: 1H NMR (500 MHz, CDCl3) δ 7.83 (br s, 1H), 7.47-7.32 (m, 5H), 6.77 (d, J=8.8 Hz, 1H), 6.60 (br s, 2H), 6.06 (d, J=8.8 Hz, 1H), 5.51 (br s, 1H), 5.04 (s, 2H), 3.85 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography
  10. washeluting with 0-10% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-57c23484125c4aeb8525e7e9b8c4fbd6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278940B2

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