Nitric Acid → HCID 20750069, compound

HRID 897295Notes

Reaction equation

HRID 897295 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N+:3]=1[O-:11].[N+:12]([O-])([OH:14])=[O:13].[OH-].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=[C:4]([CH3:10])[N+:3]=1[O-:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium Hydroxide2×HCID 20750068HCID 20750068, compound

Product 1

HCID 20750069HCID 20750069, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 124C (7.0 g, 32.4 mmol) in concentrate H2SO4 (9.5 mL) was added to a solution of concentrate H2SO4 (9.5 mL) and fuming HNO3 (13 mL) and the mixture was heated at 60° C. for 30 min. After cooling to room temperature, the reaction mixture was added to iced 6M solution of NaOH (150 mL) and neutralized to pH 6 with 1N NaOH solution. The reaction mixture was extracted with dichloromethane (4×100 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated to give 124D as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe reaction mixture was extracted with dichloromethane (4×100 mL)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1761a2b84e734f1396262ad5cbda5bab
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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