Hydrochloric Acid → HCID 53793436, compound

HRID 344927Notes

Reaction equation

HRID 344927 reaction equation
[C:1]([C:4]1[C:5]([OH:25])=[C:6]([CH2:22][CH:23]=[CH2:24])[CH:7]=[C:8]([C:10]2[C:11]([OH:21])=[C:12]([CH2:18][CH:19]=[CH2:20])[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=2)[CH:9]=1)(=O)[CH3:2].[CH3:26][NH2:27].B.[Na].Cl.C(=O)([O-])O.[Na+]>O.CO>[CH2:18]([C:12]1[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=[C:10]([C:8]2[CH:9]=[C:4]([CH:1]([NH:27][CH3:26])[CH3:2])[C:5]([OH:25])=[C:6]([CH2:22][CH:23]=[CH2:24])[CH:7]=2)[C:11]=1[OH:21])[CH:19]=[CH2:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 54205987HCID 54205987, compoundHCID 178418435HCID 178418435, compound2×

Product 1

HCID 53793436HCID 53793436, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution was prepared by dissolving 0.10 g of 5'-acetyl-3,3'-diallyl-5-ethyl-2,4'-biphenyldiol into 2 ml of 40% metanol solution of methylamine. The solution was reflexed by heating for 3 hours, cooled, 0.2 g of sodium boron hydride was added thereinto, was reflexed by heating. The solution was added 0.2 g of sodium boron hydride and stirred from 1 hour at room temperature. The reaction mixture, wherein an excess of reagent was decomposed with hydrochloric acid, was neutralized with water solution of sodium hydrogencarbonate and extracted with diethylether. The extract was washed with an aqueous solution saturated with NaCl, dried with sodium sulfate and concentrated. The concentrate was purified by silica gel column-chromatography (dichloroethane:methanol=50:1) to yield 80 mg of 3,3'-diallyl-5-ethyl-5'-(1-methylaminoethyl)-2,4'-biphenyldiol.

Workup

  1. customA solution was prepared
  2. temperatureby heating for 3 hours
  3. temperaturecooled
  4. temperatureby heating
  5. extractionextracted with diethylether
  6. washThe extract was washed with an aqueous solution saturated with NaCl
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was purified by silica gel column-chromatography (dichloroethane:methanol=50:1)

Sources & evidence

ORD record
ord-8b7ead5c560b4ae9bc2021265c8787d5
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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