Methanol → HCID 15480815, compound

HRID 1058617Notes

Reaction equation

HRID 1058617 reaction equation
CO.[BH4-].[Na+].[Cl:5][C:6]1[C:15]([N+:16]([O-])=O)=[C:14]([NH:19][CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.O>O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:16][C:15]1[C:6]([Cl:5])=[N:7][C:8]2[C:13]([C:14]=1[NH:19][CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH2:23]1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydride2×HCID 18668740HCID 18668740, compound

Product 1

HCID 15480815HCID 15480815, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6.56 g of nickel chloride hexahydrate and 22.3 ml of methanol in 100 ml of tetrahydrofuran, 2.09 g of sodium borohydride was added portionwise under ice-cooling, and then a suspension of 31.9 g of 2-chloro-3-nitro-4-[2-(N-triphenylmethyl-4-piperidyl)ethylamino]quinoline in 300 ml of tetrahydrofuran was added to the mixture. Successively, 8.35 g of sodium borohydride divided in four portions was added portionwise, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with 50 ml of water and an insoluble matter was filtered off, and then the extract was concentrated. The residue was added with water and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated. The resulting pale green liquid was solidified with a mixture of ethyl acetate and diisopropyl ether, and the solid was washed successively with isopropanol and diisopropyl ether to give 20.1 g of pale green crystals. Recrystallization from isopropanol gave pale green crystals having the melting point of from 116 to 121° C.

Workup

  1. temperaturecooling
  2. additionwas added to the mixture
  3. additionwas added portionwise
  4. filtrationan insoluble matter was filtered off
  5. concentrationthe extract was concentrated
  6. additionThe residue was added with water
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed successively with water and saturated brine
  9. customdried
  10. customthe solvent was evaporated
  11. additionThe resulting pale green liquid was solidified with a mixture of ethyl acetate and diisopropyl ether
  12. washthe solid was washed successively with isopropanol and diisopropyl ether

Sources & evidence

ORD record
ord-ab7a1e396b044b2189c7c12b661d9bb7
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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