Methylhydrazine → 2-methyl-5-(p-toluenesulfonyloxy)isoquino [8,7,6-cd]indazole-6(2H)-one

HRID 440359

Reaction equation

HRID 440359 reaction equation
F[C:2]1[C:15]2[C:14](=O)[C:13]3[CH:12]=[N:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:17])[C:6]=2[C:5]([O:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(OS(C2C=CC(C)=CC=2)(=O)=O)=CC=1.[CH3:57][NH:58][NH2:59]>N1C=CC=CC=1>[C:25]1([CH3:28])[CH:26]=[CH:27][C:22]([S:19]([O:18][C:5]2[CH:4]=[CH:3][C:2]3[N:58]([CH3:57])[N:59]=[C:14]4[C:13]5[CH:12]=[N:11][CH:10]=[CH:9][C:8]=5[C:7](=[O:17])[C:6]=2[C:15]=34)(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Product 1

HCID 153378742-methyl-5-(p-toluenesulfonyloxy)isoquino [8,7,6-cd]indazole-6(2H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The 1:1 mixture of 9-fluoro-6-(p-toluenesulfonyloxy) benzo[g] isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy) benzo[g]isoquinoline-5,10-dione, of Preparative Example 10a, (0.041 g) is dissolved in dry pyridine (2 mL) and a freshly prepared 1M solution of N-methyhydrazine in pyridine (0.183 mL) is added. After stirring for three hours at room temperature the reaction mixture is concentrated to dryness and added with water (5 mL), with NaH2PO4 saturated solution (5 mL) and extracted several times with methylene chloride (50 mL). The combined organic solutions are dried ever anhydrous sodium sulfate and the solvent is removed at reduced pressure. The obtained residue is purified by silica-gel column chromatography (eluant: methylene chloride/ethyl acetate 90/10 v/v (50 mL), then 75/25 (50 mL), then 60/40 (50 mL) and finally 40/60 (50 mL) to give2-methyl-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one.

Workup

  1. concentrationis concentrated to dryness
  2. additionadded with water (5 mL), with NaH2PO4 saturated solution (5 mL)
  3. extractionextracted several times with methylene chloride (50 mL)
  4. dry with materialThe combined organic solutions are dried ever anhydrous sodium sulfate
  5. customthe solvent is removed at reduced pressure
  6. customThe obtained residue is purified by silica-gel column chromatography (eluant

Sources & evidence

ORD record
ord-3ca45260a8c847a0879fc9abd9d7a87d
Source dataset
uspto-grants-1996_05
Patent number
US05519029

Linked notes

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