Calcium Chloride → HCID 135599877, compound

HRID 1175812Notes

Reaction equation

HRID 1175812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N:10]1[CH:14]=[C:13]([C:15](O)=[O:16])[C:12]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=2[N+:27]([O-])=O)=[N:11]1.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]2[C:12]3[C:13](=[CH:14][N:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[Cl:1])[N:11]=3)[C:15](=[O:16])[NH:27][C:19]=2[CH:20]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 23153854HCID 23153854, compound

Product 1

HCID 135599877HCID 135599877, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(2-chloro-5-methoxyphenyl)-3-(2,4-dinitrophenyl)-1H-pyrazole-4-carboxylic acid (3.20 g), 90% calcium chloride (200 mg) and 90% ethanol (150 ml) was stirred at 90° C. for 10 minutes, reduced iron (5.12 g) was added thereto, and then was stirred at 90° C. for 4 hours. The reaction mixture was cooled, filtered through Celite, the Celite layer was washed ethyl acetate. The filtrate and washings were combined, added water thereto and then extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the target compound (1.20 g).

Workup

  1. stirringwas stirred at 90° C. for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. washthe Celite layer was washed ethyl acetate
  5. additionadded water
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7298479030014aaba9b1cd44054dd1cd
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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