HCID 598953, compound → HCID 15077507, compound

HRID 1074209Notes

Reaction equation

HRID 1074209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:11][C:12]2[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=2)[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1>[Ni].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([S:11][C:12]2[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 598953HCID 598953, compound

Product 1

HCID 15077507HCID 15077507, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g (10.7 mmoles) of the product from Example 49, 1.5 spatulas of Raney nickel and 200 ml of ethanol was hydrogenated at 1 atmosphere and room temperature for 18 hours. An additional spatula of Raney nickel was added and hydrogenation continued for 90 minutes. The mixture was filtered to remove the catalyst and the filtrates concentrated. The residue was recrystallized from dichloromethane/petroleum ether (bp 30°-60° C.) to give the product as colorless plates (1.7 g, 66%), mp 116°-120° C.

Workup

  1. waithydrogenation continued for 90 minutes
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrates concentrated
  5. customThe residue was recrystallized from dichloromethane/petroleum ether (bp 30°-60° C.)
  6. customto give the product as colorless plates (1.7 g, 66%), mp 116°-120° C.

Sources & evidence

ORD record
ord-55efacb258cf4beda7a88eaa1d3cc206
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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