HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethylformamide → 3-(2-Methoxyphenoxy)-2-nitro-5-(pyridin-3-yloxy)-aniline

HRID 13245
Notes
Print preview

Reaction equation

HRID 13245 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.F[C:20]1[CH:21]=[C:22]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[C:23]([N+:27]([O-:29])=[O:28])=[C:24]([CH:26]=1)[NH2:25]>C(OCC)(=O)C>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[O:30][C:22]1[C:23]([N+:27]([O-:29])=[O:28])=[C:24]([CH:26]=[C:20]([O:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:21]=1)[NH2:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 231454335-Fluoro-3-(2-methoxyphenoxy)-2-nitroaniline

Product 1

HCID 231451253-(2-Methoxyphenoxy)-2-nitro-5-(pyridin-3-yloxy)-aniline

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
90 °C

Procedure

1.24 g of 3-hydroxypyridine and 5.42 g of potassium carbonate were added to a dimethylformamide (30 ml) solution of 3.03 g of 5-fluoro-3-(2-methoxyphenoxy)-2-nitroaniline, and the reaction liquid was stirred overnight at 90° C. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and then dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1 to 1/2) to obtain the entitled compound as an orange solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1 to 1/2)

Sources & evidence

ORD record
ord-8c7fa5a2cf3b4f4696863b7655a33295
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes