HCID 10679924, compound → HCID 10654574, compound

HRID 1768757Notes

Reaction equation

HRID 1768757 reaction equation
[NH2:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[N+:12]([O-])=O>[Ni].CO>[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[NH2:12]

Participants

4

Reactant 1

HCID 10679924HCID 10679924, compound

Product 1

HCID 10654574HCID 10654574, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5.00 g of Compound 4 obtained in the above step (4) and 12.9 g of Raney nickel in methanol is hydrogenated at ordinary temperature under atmospheric pressure. The catalyst is filtered off, and the filtrate is concentrated in vacuo to remove the solvent. The residue is chromatographed on an alumina column, eluting with 5% methanol/chloroform. The product is recrystallized from methylene chloride-ethyl acetate to give 3.37 g of the titled compound (IIla) as crystals. Yield: 86%

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto remove the solvent
  4. customThe residue is chromatographed on an alumina column
  5. washeluting with 5% methanol/chloroform
  6. customThe product is recrystallized from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-536e5686bdac425ebadf9ceec69a0356
Source dataset
uspto-grants-1995_01
Patent number
US05378848

Reaction notes

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