Hydrochloric Acid → HCID 21183750, compound

HRID 1384808Notes

Reaction equation

HRID 1384808 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:14]=[C:15]([C:16](OC)=[O:17])[C:5]=3[C:4]=2[CH:3]=1.[BH4-].[Na+].CO.Cl>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:26])[N:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:14]=[C:15]([CH2:16][OH:17])[C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 21183738HCID 21183738, compound

Product 1

HCID 21183750HCID 21183750, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17.2 g (47 mmol) of methyl 8-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate, of 8.7 g (230 mmol) of sodium borohydride and of 9.4 ml (230 mmol) of methanol in 300 ml of tetrahydrofuran is heated at reflux for 4 h. The mixture is cooled and poured onto a stirred solution of 100 ml of 2N hydrochloric acid and 100 ml of dichloromethane. The precipitate is collected by filtration, washed with water and dichloromethane and dried under reduced pressure. 15 g (44 mmol) of solid are obtained.

Workup

  1. temperatureat reflux for 4 h
  2. temperatureThe mixture is cooled
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water and dichloromethane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-faa03cdee6764a0b9626376db119ca2e
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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