HCID 21428943, compound → HCID 21428880, compound

HRID 437664Notes

Reaction equation

HRID 437664 reaction equation
[Cl:1][C:2]1[C:3]([N+:32]([O-])=O)=[CH:4][C:5]([O:30][CH3:31])=[C:6]([CH:29]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH2:28][CH2:27][C:15]2([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][NH:17][C:16]2=[O:26])[CH2:14][CH2:13]1)=[O:8].[H][H]>[Ni].C(O)(=O)C>[NH2:32][C:3]1[C:2]([Cl:1])=[CH:29][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:18][NH:17][C:16]3=[O:26])[CH2:27][CH2:28]2)=[O:8])=[C:5]([O:30][CH3:31])[CH:4]=1

Participants

5

Reactant 2

HCID 21428943HCID 21428943, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21428880HCID 21428880, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 6 parts of 5-chloro-2-methoxy-4-nitro-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5] dec-8-yl)ethyl]benzamide in 150 parts of acetic acid is hydrogenated at normal pressure and at room temperature with 1 part 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 taken up in water and the whole is alkalized. The precipitated product is filtered off and crystallized twice from ethanol, yielding 1.7 parts of 4-amino-5-chloro-2-methoxy-N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]-dec-8-yl)ethyl]benzamide; mp. 247.4° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. filtrationThe precipitated product is filtered off
  4. customcrystallized twice from ethanol

Sources & evidence

ORD record
ord-0d8651c7d3e44633823e1f37e7956e3a
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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