Methanol → 7-Chloro-1-(hydroxymethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one

HRID 1384835Notes

Reaction equation

HRID 1384835 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:17]([C:18](OCC)=[O:19])=[N:16][N:15]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:14](=[O:29])[C:9]=3[N:10]([CH3:13])[C:11]=2[CH:12]=1.CO>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:17]([CH2:18][OH:19])=[N:16][N:15]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:14](=[O:29])[C:9]=3[N:10]([CH3:13])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 15461900Ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

Product 1

HCID 154619017-Chloro-1-(hydroxymethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-oneYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (66.1 mmol) of sodium borohydride are added to a solution of 4.04 g (10.6 mmol) of ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-carboxylate in 150 ml of tetrahydrofuran. 2.25 ml of methanol are gradually added, with stirring, and then the mixture is heated at reflux for 5 hours. The mixture is poured onto an ice-cold 1 M hydrochloric acid solution and an insoluble product is separated by filtration on sintered glass, which product is washed with water and with diethyl ether and then dried. 3.3 g (9.7 mmol) of compound are isolated in the form of a white solid which is used as is in the following stage.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 5 hours
  3. customan insoluble product is separated by filtration on sintered glass, which product
  4. washis washed with water and with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-799d9486c3864a37bdfc4efdd87d77d1
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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