Sulfuric Acid → HCID 68322517, compound

HRID 59942Notes

Reaction equation

HRID 59942 reaction equation
OS(O)(=O)=O.N[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[CH2:15][CH3:16].N([O-])=[O:18].[Na+]>O>[CH2:15]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:7]=1[OH:18])[C:11]#[N:12])[CH3:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 27353304-Amino-3-ethylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 68322517HCID 68322517, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Concentrated H2SO4 (3.4 mL) was added dropwise to a solution of 4-amino-3-ethylbenzonitrile (6.84 mmol) in H2O (12 mL) at 0° C. A solution of NaNO2 (7.52 mmol) in H2O (5 mL) was added dropwise at 0° C. to the resulting mixture. The reaction was stirred at 0° C. for 30 min and at 100° C. for 2 h. The mixture was cooled to room temperature and extracted with EtOAc. The organic layer was washed (H2O), dried and concentrated to yield the desired product.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed (H2O)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33b4df3f08864a06bc6dd8ba3ccfe5e1
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

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