Potassium Carbonate → HCID 22285195, compound

HRID 2099849Notes

Reaction equation

HRID 2099849 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].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N+:9]([C:3]1[CH:4]=[C:5]([O:8][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 22285195HCID 22285195, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Into a DMF solution (150 ml) containing 4-amino-3-nitrophenol (4.72 g) were added successively potassium carbonate (12.8 g), tetrabutylammonium iodide (0.56 g) and 3-chloromethylpyridine hydrochloride (5.42 g), followed by about 1.5 hours of heating at 60° C. The reaction solution was concentrated under reduced pressure, ice-water (250 ml) and 1M hydrochloric acid aqueous solution (30 ml) were poured thereto, and the formed crystals were collected by filtration and dried to obtain 2-nitro-4-(pyridin-3-ylmethoxy)aniline (7.39 g). Hereinafter, the compounds of Reference Examples 35 and 60 were obtained similarly.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, ice-water (250 ml) and 1M hydrochloric acid aqueous solution (30 ml)
  2. additionwere poured
  3. filtrationthe formed crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-315cc1379e884cfb9fd8130525fb04ba
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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