1-(6-Fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid → HCID 23339760, compound

HRID 28228Notes

Reaction equation

HRID 28228 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:9]2[C:24]([OH:26])=O)[C:5]([N+:27]([O-])=O)=[CH:4][CH:3]=1>[Fe].C(O)(=O)C>[C:14]([N:11]1[CH2:12][CH2:13][N:8]2[C:6]3[N:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[NH:27][C:24](=[O:26])[CH:9]2[CH2:10]1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

4

Reactant 1

HCID 233397701-(6-Fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid

Product 1

HCID 23339760HCID 23339760, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 14.0 g. of 1-(6-fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid in 300 ml. of acetic acid is added, while stirring, 7.0 g. of iron powder. The mixture is warmed to 55° for 3 hours then concentrated. The residue is treated with water and extracted with methylene chloride, dried (MgSO4) and concentrated. The residue is placed on a dry column of alumina and eluted with chloroform. The product band in the column is cut out and the product is washed from the alumina with methanol. Concentration of the methanol wash gives 5.0 g. of the light green-colored title product. Recrystallization from ethanol gives 2.2 g. of pure product, m.p. 210°-214°.

Workup

  1. temperatureThe mixture is warmed to 55° for 3 hours
  2. concentrationthen concentrated
  3. additionThe residue is treated with water
  4. extractionextracted with methylene chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washeluted with chloroform
  8. washthe product is washed from the alumina with methanol
  9. washConcentration of the methanol wash
  10. customgives 5.0 g

Sources & evidence

ORD record
ord-cc3c3ed720e14e38846001824a45b408
Source dataset
uspto-grants-1980_09
Patent number
US04225713

Reaction notes

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