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Phosphorus oxide (P4O10) → 3,5-Diphenyl-1H-pyrazolo[4,3-c]isoquinoline

HRID 719256
Notes
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Reaction equation

HRID 719256 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[C:25]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[C:15]1([C:21]2[C:25]3[N:26]=[C:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:24]=3[NH:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 12094555HCID 12094555, compound

Product 1

HCID 100874193,5-Diphenyl-1H-pyrazolo[4,3-c]isoquinoline

Reagents, catalysts & solvents 1

HCID 7237
O-Xylene
Solvent

Conditions

Temperature
150 °C

Procedure

201 mg of phosphorus pentoxide were added to a solution of 240 mg of N-(3,5-diphenyl-1H-pyrazol-4-yl)benzylamine (2) in 10 ml of xylene, after which 195 μl of phosphorus oxychloride were added dropwise at 150° C. The reaction solution was stirred at 150° C. for 4 h and then stirred at RT for 12 h; a saturated solution of sodium hydrogen carbonate was then added and the whole was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained:

Workup

  1. stirringstirred at RT for 12 h
  2. extractionthe whole was extracted with methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  6. customThe following was obtained

Sources & evidence

ORD record
ord-5166420dc8a44daaac79f9b02ea9447e
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07132428B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes