Nitric Acid → HCID 20292624, compound

HRID 1413047Notes

Reaction equation

HRID 1413047 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[N+:16]([O-])([OH:18])=[O:17].O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 13336642HCID 13336642, compound

Product 1

HCID 20292624HCID 20292624, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(5-chloro-2-pyrimidyloxy)phenol (1.4 g) in acetic acid (20 ml) was treated with fuming nitric acid (0.5 g) at 25° C. After 4 hours the mixture was poured into water and extracted with chloroform (2×100 ml). The chloroform extracts were dried (Mg2O4) and evaporated to a yellow solid which was chromatographed on silica gel (40 g). Elution with chloroform gave 4-(5-chloro-2-pyrimidyloxy)-2-nitrophenol (0.9 g) as pale yellow crystals.

Workup

  1. extractionextracted with chloroform (2×100 ml)
  2. dry with materialThe chloroform extracts were dried (Mg2O4)
  3. customevaporated to a yellow solid which
  4. customwas chromatographed on silica gel (40 g)
  5. washElution with chloroform

Sources & evidence

ORD record
ord-881dd1f38cb84ffbac6014592fe95e5e
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

Loading…