HCID 19990418, compound → HCID 19990457, compound

HRID 346166Notes

Reaction equation

HRID 346166 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=[O:11])[C:7]([NH:13][C:14]([C:16](OCC)=[O:17])=[O:15])=[CH:6][C:5]=1[C:21]#[N:22])(=[O:3])[CH3:2]>CN(C)C=O.[Pt]>[C:1]([C:4]1[CH:9]=[C:8]2[C:7]([NH:13][C:14](=[O:15])[C:16](=[O:17])[N:10]2[OH:11])=[CH:6][C:5]=1[C:21]#[N:22])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19990418HCID 19990418, compound

Product 1

HCID 19990457HCID 19990457, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-acetyl-2-cyano-4-ethoxalylamino-5-nitrobenzene (0.31 g, 1 mmol) in 10 ml of N,N-dimethylformamide was hydrogenated at atmospheric pressure and room temperature for 1 h in the presence of 30 mg of 5% platinum on carbon. The catalyst was filtered off, and the filtrate was evaporated to dryness. The pure product was obtained after recrystallization from water with decolourising charcoal. Yield 0.12 g (49%). M.p. 340.8° C. decomp. (DSC); IR (KBr): 2238 (CN), 1692 cm-1 ; 1H-NMR (DMSO-d6): 2.62 (s, 3H, CH3), 7.43 (s, 1H, ArH), 7.96 (s, 1H, ArH), ca. 12 (very broad s, 2H, NH and OH); MS m/e: 245 (M+, 26%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe pure product was obtained
  4. customafter recrystallization from water with decolourising charcoal

Sources & evidence

ORD record
ord-410a92e7640f4f0db3ffef64b701a0d0
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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