Water → HCID 178515565, compound

HRID 643339Notes

Reaction equation

HRID 643339 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12](=[O:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:22]([O-])=O.[Na+].O>CC(O)=O.OS(O)(=O)=O>[CH2:14]([C:13]1[N:22]=[N:1][C:2]2[C:3]([C:12]=1[OH:21])=[CH:4][CH:5]=[CH:6][C:7]=2[C:8]([F:9])([F:10])[F:11])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 685791181-(2-Amino-3-trifluoromethyl-phenyl)-3-phenyl-propan-1-one

Product 1

HCID 178515565HCID 178515565, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(2-amino-3-trifluoromethyl-phenyl)-3-phenyl-propan-1-one (4.2 g, 13.8 mmol) in AcOH (70 ml) and H2SO4 (10 ml) was added a solution of NaNO2 (1.8 g in 10 ml H2O). The reaction was then heated to 70° C. After 1.5 hr, the reaction was cooled, poured into water and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to give 3-benzyl-8-trifluoromethyl-cinnolin-4-ol

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dca9a4535cc44a9fbef1f4f1812445ee
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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