Nitric Acid → HCID 20472940, compound

HRID 2295952Notes

Reaction equation

HRID 2295952 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[N:10][CH:11]=1.O.C(Cl)(Cl)Cl>C(OCC)C>[N+:1]([C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[N:10]=[CH:11][C:6]([Cl:5])=[CH:7][N:8]=2)=[CH:14][C:15]=1[OH:19])([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 6212ChloroformHCID 132098113-[(5-Chloropyrimidin-2-yl)oxy]phenol

Product 1

HCID 20472940HCID 20472940, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Fuming nitric acid (1.3 g) was added slowly to a stirred suspension of 3-(5-chloro-2-pyrimidyloxy)phenol (2.2 g) in diethyl ether (20 ml) at 20° C. The temperature rose to 30° C. and the resultant orange solution was allowed to stand for 48 hr before the addition of water and extraction with chloroform (100 ml). The chloroform extracts were dried and evaporated to give a pale yellow crystalline solid (1.3 g). Chromatography on a column of silica gel (80 g) with chloroform elution gave the title compound as a pale yellow-solid from the first fraction (0.7 g, 28%). The compound was identified from its pmr spectrum.

Workup

  1. customrose to 30° C.
  2. dry with materialThe chloroform extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-1a77e2f7b9784622aeeb151335f61d25
Source dataset
uspto-grants-1984_01
Patent number
US04427437

Reaction notes

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