Nitric Acid → HCID 49820316, compound

HRID 1914800Notes

Reaction equation

HRID 1914800 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[C:18]4[CH:19]=[C:20]([OH:25])[C:21]([Br:24])=[C:22]([Br:23])[C:17]=4[O:16][CH:15]=3)=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N+]([O-])(O)=[O:27].O>CC(O)=O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[C:18]4[C:19](=[O:27])[C:20](=[O:25])[C:21]([Br:24])=[C:22]([Br:23])[C:17]=4[O:16][CH:15]=3)=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 66646980HCID 66646980, compound

Product 1

HCID 49820316HCID 49820316, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-(1H-imidazol-1-yl)phenyl)(6,7-dibromo-5-hydroxybenzofuran-3-yl)methanone (55 mg, 0.119 mmol) in AcOH (1 mL) was added nitric acid—69% (36.7 μl, 0.595 mmol) at room temperature. The mixture was heated to 60° C. for 1 hour then cooled to room temperature, poured onto iced water (3 mL) and the suspension filtered under vacuum to furnish 42 mg of a red/orange solid. 1H NMR (DMSO-d6) was consistent with two species—product and starting material. The material was re-subjected to the above conditions for a further hour and then worked up as before to afford compound x (25 mg, 44%).

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationthe suspension filtered under vacuum

Sources & evidence

ORD record
ord-96f666a4e3544736a99be53261293081
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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