1-(2-Hydrazinylethyl)pyrrolidine → 9-Methoxy-5-nitro-2-[2-(1-pyrrolidinyl)ethyl]-2H-[1]-benzopyrano[4,3,2-cd]indazole, monohydrochloride

HRID 364167

Reaction equation

HRID 364167 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=3)[O:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[NH:22]([CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[NH2:23]>C1COCC1>[ClH:1].[CH3:18][O:17][C:11]1[CH:10]=[CH:9][C:8]2[O:7][C:6]3[C:15]4[C:14](=[N:23][N:22]([CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)[C:2]=4[CH:3]=[CH:4][C:5]=3[N+:19]([O-:21])=[O:20])[C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 30315561-(2-Hydrazinylethyl)pyrrolidineHCID 136890881-Chloro-7-methoxy-4-nitro-9H-xanthen-9-one

Product 1

HCID 1317148059-Methoxy-5-nitro-2-[2-(1-pyrrolidinyl)ethyl]-2H-[1]-benzopyrano[4,3,2-cd]indazole, monohydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 12.2 g of 1-chloro-7-methoxy-4-nitro-9H-xanthen-9-one and 11.0 g of 1-(2-hydrazinoethyl)pyrrolidine in 200 ml of THF was stirred 20 hours at room temperature. The orange liquor was decanted, freed of solvent under reduced pressure, and the residue, in chloroform, was chromatographed over silica gel, eluting with chloroform-methanol (25:1 by volume). The desired fractions yielded the free base of the title compound, mp 140°-142° C.

Workup

  1. customThe orange liquor was decanted
  2. customthe residue, in chloroform, was chromatographed over silica gel
  3. washeluting with chloroform-methanol (25:1 by volume)

Sources & evidence

ORD record
ord-89315955443e42b683b57d0ac48944ff
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Linked notes

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