Hydrochloric Acid → HCID 54483394, compound

HRID 1072898Notes

Reaction equation

HRID 1072898 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][N:15]([CH3:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].Cl.C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][N:15]([CH3:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22388484HCID 22388484, compound

Product 1

HCID 54483394HCID 54483394, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (58 mg) was added to a solution of 2-chloro-4-((2-(N-methyl-N-(2-pyridinyl)amino)ethyl)oxy)benzaldehyde (438 mg) in ethanol (3 ml) at room temperature and the mixture was stirred for 2 hr. 1N Hydrochloric acid (1.5 ml) was dropwise added to the reaction mixture to decompose the redundant reagent and the whole mixture was diluted with ethyl acetate. A saturated aqueous solution of sodium hydrogencarbonate was added to neutralize the mixture and the resulting product was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the objective compound (437 mg) as a colorless oil.

Workup

  1. extractionthe resulting product was extracted twice with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c2867192c52e4508a5217e4e9afde244
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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