Nitric Acid → HCID 94920062, compound

HRID 925116Notes

Reaction equation

HRID 925116 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:19]([O-])([OH:21])=[O:20]>CC(O)=O.CC(OC(C)=O)=O>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:11]2([C:17]#[N:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[C:6]([N+:19]([O-:21])=[O:20])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 46393531-(3,4-Dimethoxyphenyl)cyclohexanecarbonitrile

Product 1

HCID 94920062HCID 94920062, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Conditions

Temperature
0 °C

Procedure

1-(3,4-Dimethoxyphenyl)cyclohexanecarbonitrile (0.736 g, 3 mmol), prepared in Step 1, was dissolved in HOAc/Ac2O 1/1 (6 mL) was cooled to 0° C. and treated slowly with nitric acid (0.582 g, 6 mmol, 65%). The reaction was left stirring in the ice bath for 10 min, poured into ice and extracted with EtOAc. Organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded (251 mg, 29%) of 1-(4,5-dimethoxy-2-nitrophenyl)cyclohexanecarbonitrile. MS (ESI) m/z 291 (M+H)+.

Workup

  1. waitThe reaction was left
  2. additionpoured into ice
  3. extractionextracted with EtOAc
  4. dry with materialOrganic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-6ec5b9978a574aa4be75df8b70379e70
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

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