Nitric Acid → HCID 11670736, compound

HRID 1693497Notes

Reaction equation

HRID 1693497 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:4][CH:3]=1.[N+:32]([O-:35])([OH:34])=[O:33]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[N+:32]([O-:34])=[O:33])[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[CH:20][C:21]([N+:32]([O-:35])=[O:33])=[CH:22][CH:23]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 11525617HCID 11525617, compound

Product 2

HCID 11670736HCID 11670736, compoundHCID 11677920HCID 11677920, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (50 mg, 0.104 mmol) is dissolved in 5 mL of acetic anhydride. Concentrated nitric acid (300 μL) is added dropwise over 2 minutes. After the reaction mixture is stirred for 15 minutes, the voiatiles are stripped off and the resulting crude material is purified by column chromatography to give 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(2-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one and 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(4-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. customthe resulting crude material is purified by column chromatography

Sources & evidence

ORD record
ord-09f6d4c5ef4c48b783d106ccd74a8eea
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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