Pyridine → HCID 135621732, compound

HRID 1783301Notes

Reaction equation

HRID 1783301 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.N1C=CC=CC=1.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:15][C:12]1[CH:11]=[CH:10][C:9]2[C:3]3[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=3[NH:1][C:23](=[O:25])[C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 94429TriphosgeneHCID 6451240Aluminum(III) ChlorideHCID 23084651HCID 23084651, compound

Product 1

HCID 135621732HCID 135621732, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 5-amino-4-(4-fluorophenyl)-1,3-dimethylpyrazole (20.0 g) and pyridine (23.6 mL) in dichloromethane (150 mL) was added dropwise over 30 min to a solution of triphosgene (11.6 g) in dichloromethane (100 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. The reaction solution was added dropwise to a solution of aluminum chloride (97.5 g) in dichloromethane under ice-cooling, and the mixture was stirred at room temperature for 2 days. After the completion of the reaction, the reaction solution was poured into ice-water. The precipitated crystals were collected by filtration and washed with water to give 7-fluoro-1,3-dimethyl-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one (13.2 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 days
  4. customAfter the completion of the reaction
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-b0de85afc5504ce0a68ce8a449cd283a
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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