Reaktion #72753

ord-05be219954e84e998756ab0b54497e7c

Reaktionsgleichung

COc1cc(Br)cc([N+](=O)[O-])c1N
4-bromo-2-methoxy-6-nitrobenzenamine
O=S(=O)(O)O
H2SO4
CC(=O)O
HOAc
→
COc1cc(Br)cc([N+](=O)[O-])c1NC(C)=O
desired product
Ausbeute 75.0%
COc1cc(Br)cc([N+](=O)[O-])c1NC(C)=O
N-(4-bromo-2-methoxy-6-nitrophenyl)acetamide
Ausbeute 75.0%

Edukte

COc1cc(Br)cc([N+](=O)[O-])c1N
4-bromo-2-methoxy-6-nitrobenzenamine
O=S(=O)(O)O
H2SO4
CC(=O)O
HOAc

Reagenzien

Keine

Lösungsmittel

CC(=O)OC(C)=O
Ac2O

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITkept at rt overnight
  2. 2
    FiltrationThe formed precipitate was collected by filtration
  3. 3
    Waschenwashed with hexane

Vorschrift

To a solution of 4-bromo-2-methoxy-6-nitrobenzenamine (27.85 g) in HOAc (150 mL) and Ac2O (17 mL) was added conc. H2SO4 at 70° C. and the mixture was stirred at 70° C. for 30 min and kept at rt overnight. The formed precipitate was collected by filtration and washed with hexane to afford the desired product as a light yellow solid (24.45 g, 75%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.01 (s, 3H), 3.92 (s, 3H), 7.61 (d, 1H, J=1.8 Hz), 7.65 (d, 1H, J=1.8 Hz), 9.91 (s, 1H); LC-MS: m/e=289 [M+1]+

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541411B2uspto-grants-2013_09