HCID 19867711, compound → HCID 19867706, compound

HRID 1198945Notes

Reaction equation

HRID 1198945 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[C:7]([CH3:15])[CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[NH:5][C:4](=[O:16])[CH2:3]1>C(O)C.[Ni]>[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[C:7]([CH3:15])[CH:8]=[C:9]([NH2:12])[CH:10]=2)[NH:5][C:4](=[O:16])[CH2:3]1

Participants

4

Reactant 1

HCID 19867711HCID 19867711, compound

Product 1

HCID 19867706HCID 19867706, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 3,4-dihydro-4,4-dimethyl-6-nitro-8-methyl-2-(1H)-quinolone (9.46 g) in absolute ethanol (80 cm3) was hydrogenated at 60° and 60 p.s.i. (4.13×105Pa) pressure over Raney nickel (0.9 g) for 6 hours. The cooled solution was then filtered through "Solkafloc" (Trade mark for a cellulose based filtering aid) and evaporated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:chloroform, 1:33 by volume. Combination and evaporation of appropriate fractions gave the title compound (3.17 g) which was characterised spectroscopically and used directly in Preparation 22 without further purification.

Workup

  1. customwas hydrogenated at 60°
  2. filtrationThe cooled solution was then filtered through "Solkafloc" (Trade mark for a cellulose
  3. filtrationbased filtering aid) and
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  7. washeluting with methanol
  8. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-bd90a94980054809885b8800838e55c6
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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