Hydrazine hydrate (1:1) → 3-Amino-2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino]-5-(pyrid-3-ylmethyl)pyridine

HRID 1607040

Reaction equation

HRID 1607040 reaction equation
O.NN.[N:4]1[C:13]2[CH:12]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[C:23]([N+:24]([O-])=O)=[CH:22][C:21]([CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[CH:20][N:19]=3)[CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1>CO.[Ni]>[NH2:24][C:23]1[C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH:12]2[C:13]3[N:4]=[CH:5][CH:6]=[CH:7][C:8]=3[CH2:9][CH2:10][CH2:11]2)=[N:19][CH:20]=[C:21]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 198517973-(5,6,7,8-Tetrahydroquinol-8-yl)propylamino-3-nitro-5-(pyrid-3-ylmethyl)pyridine

Product 1

HCID 198517883-Amino-2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino]-5-(pyrid-3-ylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

Hydrazine hydrate (7 ml) in methanol (25 ml) was added with stirring over 25 minutes to a cooled (5-10° C.) solution of 2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino-3-nitro-5-(pyrid-3-ylmethyl)pyridine (6.1 g) in methanol (300 ml) containing Raney Nickel (ca. 12 g). The solution was stirred for a further hour at 5° C., the catalyst was removed by filtration and the filtrate was concentrated to dryness in vacuo giving the title compound as an orange oil (theoretical yield assumed) which was used unpurified in the next reaction.

Workup

  1. stirringThe solution was stirred for a further hour at 5° C.
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ccc48eebe17d4e48bbdc02d07ca57010
Source dataset
uspto-grants-1989_09
Patent number
US04863933

Linked notes

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