Nitric Acid → HCID 12902855, compound

HRID 262248Notes

Reaction equation

HRID 262248 reaction equation
Br[C:2]1[O:3][C:4]2[C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:26]([O-])([OH:28])=[O:27].N([O-])=O.[Na+].O>C(O)(=O)C>[C:7]1([C:6]2[C:5]3[CH:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:4]=3[O:3][C:2]=2[N+:26]([O-:28])=[O:27])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 12902854HCID 12902854, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12902855HCID 12902855, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6 g. (0.018 mole) of the product of step E in hot acetic acid is treated with 6 ml. of 70 percent nitric acid while the solution is maintained at about 80° C. Sodium nitrite (2.7 g., 2 equivalents) is added gradually, and the mixture is heated on a steam bath for 45 minutes. The mixture is then poured into 500 ml. of water. The solid is filtered, recrystallized twice from acetone, then from an ethyl acetate-hexane mixture to provide yellow crystals of 3,5-diphenyl-2-nitrobenzofuran-7-carboxylic acid, m.p. 207°-209° C.

Workup

  1. temperaturethe mixture is heated on a steam bath for 45 minutes
  2. additionThe mixture is then poured into 500 ml
  3. filtrationThe solid is filtered
  4. customrecrystallized twice from acetone

Sources & evidence

ORD record
ord-1c1d6af20b414996aabd917096780e5a
Source dataset
uspto-grants-1979_05
Patent number
US04153721

Reaction notes

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