Hydrochloric Acid → 3-Benzyl-4-phenyl-8-(trifluoromethyl)cinnoline

HRID 643287Notes

Reaction equation

HRID 643287 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:17]=2[NH2:26])=[CH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N+:28]([O-])([O-])=O.[Na+].[OH-].[NH4+]>C(O)(=O)C.O>[CH2:9]([C:8]1[N:28]=[N:26][C:17]2[C:16]([C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:21][CH:20]=[CH:19][C:18]=2[C:22]([F:24])([F:25])[F:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24268Sodium NitrateHCID 685793302-(1,3-Diphenyl-propenyl)-6-trifluoromethyl-phenylamine

Product 1

HCID 116391693-Benzyl-4-phenyl-8-(trifluoromethyl)cinnoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

2-(1,3-Diphenyl-propenyl)-6-trifluoromethyl-phenylamine (0.08 g, 0.23 mmol) was dissolved in 5 mL of acetic acid, 4 mL of conc. hydrochloric acid in an ice bath. The mixture was treated with 2.5% of sodium nitrate in water. After addition the reaction was heated to ˜40° C. for 20 min, basified with ammonium hydroxide, and extracted with diethyl ether. The combined organics was dried over MgSO4 and concentrated. The material was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 2.1.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a brown solid. MS (ESI) m/z 365.

Workup

  1. additionAfter addition the reaction
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organics was dried over MgSO4
  4. concentrationconcentrated
  5. customThe material was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 2.1.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min)
  6. customThe product was collected
  7. custombased on UV absorption
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1550d3db0f62452f9095932ec9935c9b
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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