Methanol → HCID 21428955, compound

HRID 437629Notes

Reaction equation

HRID 437629 reaction equation
[ClH:1].[F:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:29][CH2:28][C:15]3([N:19]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:18][NH:17][C:16]3=[O:27])[CH2:14][CH2:13]2)=[O:8])=[C:5]([N+:32]([O-])=O)[CH:4]=1.CO.[H][H]>[Ni].O>[OH2:8].[ClH:1].[NH2:32][C:5]1[CH:4]=[C:3]([F:2])[CH:31]=[CH:30][C:6]=1[C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH2:29][CH2:28][C:15]2([N:19]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH2:18][NH:17][C:16]2=[O:27])[CH2:14][CH2:13]1)=[O:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 21428888HCID 21428888, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21428955HCID 21428955, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of 8 parts of 4-fluoro-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}-2-nitrobenzamide hydrochloride, 120 parts of methanol and 25 parts of water is hydrogenated at normal pressure and at room temperature with 5 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is crystallized from methanol. The product is filtered off and recrystallized from ethanol, yielding 1 part of 2-amino-4-fluoro-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl]ethyl}benzamide hydrochloride hydrate; mp. 223.5° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from methanol
  4. filtrationThe product is filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-171e8cc3ab524b218800171d86c2fd9c
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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