HCID 20517738, compound → HCID 20517711, compound

HRID 2198874Notes

Reaction equation

HRID 2198874 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:27])=[C:6]([CH:26]=1)[C:7]([N:9]([CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)=[O:8]>C(OC(=O)C)C.[Ni].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:27])=[C:6]([CH:26]=1)[C:7]([N:9]([CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])=[O:8]

Participants

5

Reactant 1

HCID 20517738HCID 20517738, compound

Product 1

HCID 20517711HCID 20517711, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 32.4 g 5-chloro-2-fluoro-N-(1-methyl-4-piperidinyl)-N-(2-nitrophenyl)-benzamide in 700 ml acetic acid ethyl ester and 2 to 3 g Raney nickel is hydrogenated at room temperature and normal pressure. The precipitated product is dissolved in methanol under warming and the catalyst is filtered off. The filtrate is evaporated and the crystalline residue suspended in ether and filtered, to give the heading compound, m.p. 179°-182°.

Workup

  1. customis hydrogenated at room temperature
  2. temperatureunder warming
  3. filtrationthe catalyst is filtered off
  4. customThe filtrate is evaporated
  5. filtrationfiltered
  6. customto give the heading compound, m.p. 179°-182°

Sources & evidence

ORD record
ord-35836669cfc54326af2b49387a83de1e
Source dataset
uspto-grants-1982_11
Patent number
US04360525

Reaction notes

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