HCID 19438794, compound → HCID 19438752, compound

HRID 1733879Notes

Reaction equation

HRID 1733879 reaction equation
[C:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=O)=[CH:13][C:12]([C:18]([F:21])([F:20])[F:19])=[C:11]([N:22]2[CH:26]=[CH:25][N:24]=[C:23]2[CH3:27])[CH:10]=1)([C:3]([O:5]CC)=O)=[O:2]>C(O)C.[Pd]>[OH:17][N:15]1[C:14]2[C:9](=[CH:10][C:11]([N:22]3[CH:26]=[CH:25][N:24]=[C:23]3[CH3:27])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[NH:8][C:1](=[O:2])[C:3]1=[O:5]

Participants

4

Reactant 1

HCID 19438794HCID 19438794, compound

Product 1

HCID 19438752HCID 19438752, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 19 g crude 4-ethoxalylamino-2-(2-methyl-1H-imidazol-1-yl)-5-nitrobenzotrifluoride in 500 ml 96% ethanol was hydrogenated in a Parr hydrogenation apparatus at 28.12 kPa (40 psi) by using 2 g 5% Pd-C as a catalyst. The catalyst plus precipitated product was filtered off and washed with ethanol. The filter cake was washed several times with 1N aqueous potassium hydroxide. The combined aqueous filtrates were added 4N hydrochloric acid to pH=4 to give the title compound (9.5 g; 58%). M.p.>300° C.

Workup

  1. customThe catalyst plus precipitated product
  2. filtrationwas filtered off
  3. washwashed with ethanol
  4. washThe filter cake was washed several times with 1N aqueous potassium hydroxide
  5. additionThe combined aqueous filtrates were added 4N hydrochloric acid to pH=4

Sources & evidence

ORD record
ord-322db3d8111c4a52a616f2928df728d8
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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