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

HRID 491639

Reaction equation

HRID 491639 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-65335709b7e648d9b0ec1adb116c1d19
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Linked notes

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