Tetrahydrofuran → HCID 131716573, compound

HRID 1032543Notes

Reaction equation

HRID 1032543 reaction equation
[ClH:1].[CH2:2]([N:5]([CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2)[CH2:3][CH3:4].O1CCCC1>CO.[Ni]>[ClH:1].[ClH:1].[CH2:20]([N:5]([CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2)[CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 131716574HCID 131716574, compound

Product 1

HCID 131716573HCID 131716573, compoundYield 117.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

600 mg of N,N-dipropyl-N- 2-(7-nitro-1H-indazol-4-yl)ethyl amine, hydrochloride, in 10 ml of methanol and 10 ml of tetrahydrofuran is hydrogenated in the presence of 0.5 g of Raney nickel. The mixture is filtered off from the catalyst, combined with ethereal hydrochloric acid, and concentrated. The residue is recrystallized from methanol/diethyl ether, yielding 360 mg of N,N-dipropyl-N- 2-(7-amino-1H-indazol-4-yl)ethyl amine, dihydrochloride, mp 214°-218° C.

Workup

  1. filtrationThe mixture is filtered off from the catalyst
  2. concentrationconcentrated
  3. customThe residue is recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-69616eda50ef48728331df85edf53dd7
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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