Water → HCID 19919517, compound

HRID 1975696Notes

Reaction equation

HRID 1975696 reaction equation
[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][C:17]3[S:20][C:21]([N+:23]([O-])=O)=[CH:22][C:16]=3[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1.O.[CH:27](Cl)(Cl)Cl.[C:31](=[O:34])([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.[Fe]>[C:31]([NH:23][C:21]1[S:20][C:17]2[CH2:18][CH2:19][N:14]([CH:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])[CH2:15][C:16]=2[CH:22]=1)(=[O:34])[CH3:27]

Participants

8

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 10340Sodium CarbonateHCID 15289926HCID 15289926, compound

Product 1

HCID 19919517HCID 19919517, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

1.85 g (5.13 mmole) of 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (prepared as described in Example 18) were dissolved in a mixture of 20 ml of acetic acid and 2 ml of acetic anhydride, and then 1.85 g of iron powder were added to the solution, whilst stirring at room temperature; the mixture was then stirred at the same temperature for 90 minutes. At the end of this time, water and chloroform were added to the reaction mixture, and the mixture was neutralized with sodium carbonate. The inorganic salt thus precipitated was filtered off, the remaining organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was then subjected to silica gel column chromatography, using a 6:4 by volume mixture of toluene and ethyl acetate as the eluent, to give 1.86 g of the title compound. This was crystallized from diisopropyl ether to obtain 1.37 g of the title compound as white crystals, melting at 155°-159° C.

Workup

  1. stirringthe mixture was then stirred at the same temperature for 90 minutes
  2. customThe inorganic salt thus precipitated
  3. filtrationwas filtered off
  4. customthe remaining organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. additionby volume mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d892b9e130fe42c0bc6f16d5c157ac21
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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