Toluene → HCID 19038242, compound

HRID 263478Notes

Reaction equation

HRID 263478 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.C1(C)C=CC=CC=1.[C:26]1([CH:32]2[CH:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[NH:35][NH:34][C:33]2=[O:43])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.C(Cl)Cl.N1C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:35]1[CH:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:33](=[O:43])[NH:34]1)=[O:12]

Participants

8

Reactant 4

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 72899Indole-2-carboxylic acidHCID 2704924,5-diphenyltetrahydro-3h-pyrazol-3-one

Product 1

HCID 19038242HCID 19038242, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Indole-2-carboxylic acid (1.35 g, 8.38 mmol), oxalyl chloride (4 mL), and DMF (3 drops) were added in order to 50 mL toluene, and stirred until gas evolution subsided and a homogeneous solution was obtained (c.20 min). Solvent was removed in vacuo, the residue taken up in CH2Cl2, and added to a solution of 4,5-diphenyl-3-pyrazolidinone (2.0 g, 8.40 mmol, 1.00 eq.) in 50 mL CH2Cl2 and 5 mL pyridine. After stirring overnight, the solution was washed with 1N HC1, dried over Na2SO4, and solvent removed in vacuo. The residual solid was stirred with CH2Cl2, filtered, and recrystallized from DMF:H2O to give 1.42 g (44%) white solid: mp 248°-50° C.

Workup

  1. customa homogeneous solution was obtained (c.20 min)
  2. customSolvent was removed in vacuo
  3. stirringAfter stirring overnight
  4. washthe solution was washed with 1N HC1
  5. dry with materialdried over Na2SO4, and solvent
  6. customremoved in vacuo
  7. stirringThe residual solid was stirred with CH2Cl2
  8. filtrationfiltered
  9. customrecrystallized from DMF

Sources & evidence

ORD record
ord-c1ef66390f68469583f104eeb4b10d59
Source dataset
uspto-grants-1997_07
Patent number
US05643926

Reaction notes

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