Potassium Carbonate → 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

HRID 491639

Reaktionsgleichung

Reaktionsgleichung von HRID 491639
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12]C([O-])(C)C.[K+].Cl[C:19]1[CH:24]=[CH:23]N=[C:21]([C:25]([NH:27][CH3:28])=[O:26])[CH:20]=1.C([O-])([O-])=O.[K+].[K+].C[NH-]>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:19]2[CH:20]=[C:21]([CH:12]=[CH:23][CH:24]=2)[C:25]([NH:27][CH3:28])=[O:26])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Komponenten

8

Edukt 5

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 37588824-Amino-3-NitrophenolHCID 21952893MethylamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 690175323-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-amino-3-nitrophenol (0.6 g, 3.84 mmol, 1.2 eq) in DMSO (2.75 mL, 5×) was treated with KOt-Bu (0.44 g, 3.84 mmol, 1.2 eq), and the mixture was stirred at RT for 2 h. The contents were treated with 4-chloro-N-methyl-2-pyridinecarboxamide (0.55 g, 3.2 mmol, 1.0 eq), K2CO3 (0.24 g, 1.7 mmol, 0.53 eq), and heated at 110° C. for 16 h. HPLC showed N-methylamide <2%. To the stirred mixture was added water (about 30 mL) slowly, and the compound precipitated. The solid was filtered off (slow filtration) and washed with water (about 60 mL). The filtrant was dried in a vacuum oven over night to give the title compound as a brown solid.

Aufarbeitung

  1. temperatureheated at 110° C. for 16 h
  2. customthe compound precipitated
  3. filtrationThe solid was filtered off
  4. filtration(slow filtration)
  5. washwashed with water (about 60 mL)
  6. customThe filtrant was dried in a vacuum oven over night

Quellen und Nachweise

ORD-Eintrag
ord-65335709b7e648d9b0ec1adb116c1d19
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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