Hydrochloric Acid → HCID 13907841, compound

HRID 2075255Notes

Reaction equation

HRID 2075255 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23].Cl.[OH-].[Na+]>CCO.O>[CH2:7]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[C:12]([N+:22]([O-:24])=[O:23])[CH:13]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 7918Acetic Anhydride2×HCID 14798Sodium HydroxideHCID 136914Benzenamine, 4-(phenylmethyl)-

Product 1

HCID 13907841HCID 13907841, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Aminodiphenylmethane (5.00 g, 27 mmol) was added in portions to acetic anhydride (26 mL, 273 mmol) with rapid stirring. A solid mass formed which was liberated by the addition of 15 mL additional acetic anhydride. The reaction was allowed to cool to ambient temp, and nitric acid (2.0 mL, 41 mmol) was added slowly dropwise via addition funnel over 30 min. The homogeneous red mixture was allowed to stir overnight and poured into a rapidly stirring solution of 30 mL water, 7 mL conc. HCl, and 24 mL EtOH (exothermic!). The reaction was allowed to cool and was then heated to reflux for ˜4 h, cooled and poured onto ice and neutralized with 10N NaOH to pH 8-9. The aqueous layer was extracted 3×DCM and dried over sodium sulfate, filtered, and concentrated. The resulting dark red oil was purified by silica gel chromatography, ISCO 120 g, 0-20% EtOAc/hexanes, to give 4-benzyl-2-nitrobenzenamine as a red oil. MS (ESI) m/z: Calculated: 228.1; Observed: 229.0 (M++1).

Workup

  1. customA solid mass formed which
  2. temperatureto cool
  3. temperaturewas then heated
  4. temperatureto reflux for ˜4 h
  5. temperaturecooled
  6. extractionThe aqueous layer was extracted 3×DCM
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting dark red oil was purified by silica gel chromatography, ISCO 120 g, 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-4ee3dcafdde5479bb600521edf6012ad
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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