2-Hydrazinoethanol → 9-methoxypyrazolo[3,4,5-kl]acridine-2(6H)-ethanol

HRID 280264Notes

Reaction equation

HRID 280264 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][NH2:5].Cl[C:7]1[C:20]2[C:19](=O)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=3)[NH:12][C:11]=2[C:10]([N+]([O-])=O)=[CH:9][CH:8]=1>CO.C1COCC1>[CH3:23][O:22][C:16]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:20]4=[C:7]([N:4]([CH2:3][CH2:2][OH:1])[N:5]=[C:19]4[C:18]=2[CH:17]=1)[CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 2

HCID 80172-HydrazinoethanolHCID 4382311-chloro-7-methoxy-4-nitro-10H-acridin-9-one

Product 1

HCID 1361665949-methoxypyrazolo[3,4,5-kl]acridine-2(6H)-ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.6 g of 2-hydroxyethyl hydrazine in 5 ml of methanol and 20 ml of THF was added over 1.5 hours to a mixture of 6.09 g of 1-chloro-7-methoxy-4-nitro-9(10H)-acridinone in 75 ml of methanol and 55 ml of THF, and the resulting suspension was stirred 20 hours at room temperature. The precipitate was collected and recrystallized from DMSO-methanol, Providing 9-methoxypyrazolo[3,4,5-kl]acridine-2(6H)ethanol, mp 275°-276° C.

Workup

  1. customThe precipitate was collected
  2. customrecrystallized from DMSO-methanol

Sources & evidence

ORD record
ord-31c3ec94d59540cbb9862113feb5b3b7
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Reaction notes

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