Calcium Chloride → HCID 135600000, compound

HRID 1175809Notes

Reaction equation

HRID 1175809 reaction equation
[NH2:1][C:2]1[N:3]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[Cl:27])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][C:9]=3[NH:8][C:7](=[O:18])[C:6]=12.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:1][C:2]1[N:3]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[Cl:27])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([NH2:15])=[CH:10][C:9]=3[NH:8][C:7](=[O:18])[C:6]=12

Participants

4

Reactant 2

HCID 5284359Calcium Chloride2×HCID 135599962HCID 135599962, compound

Product 1

HCID 135600000HCID 135600000, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-(2-chloro-5-methoxyphenyl)-7-nitro-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (0.50 g), 90% calcium chloride (0.40 g), reduced iron (1.0 g) and 90% ethanol (30 ml) was heated under reflux for 3 hours, and 90% calcium chloride (0.10 g) and reduced iron (0.27 g) was added thereto. The reaction mixture was heated under reflux for additional 8 hours. The reaction mixture was cooled and the insoluble materials were filtered off through Celite, and the filtrate was extracted with ethyl acetate. The extract was washed with a 5% sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residual solid was washed with diisopropyl ether, and dried to obtain the target compound (0.30 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for additional 8 hours
  5. temperatureThe reaction mixture was cooled
  6. filtrationthe insoluble materials were filtered off through Celite
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe extract was washed with a 5% sodium hydrogen carbonate and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washThe residual solid was washed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-27a491837b55494694f21ef22bfc8a60
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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