Methanol → HCID 67597753, compound

HRID 862531Notes

Reaction equation

HRID 862531 reaction equation
C(O)(=O)C(O)=O.[CH3:7][N:8]([CH2:10][CH2:11][O:12][CH2:13][CH:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[N+:26]([O-])=O)[CH:19]=[CH:18][CH:17]=1)[OH:15])[CH3:9].CO.[OH-].[Na+].[ClH:33].C(O)C>C(O)C.[C].[Pd].C(Cl)(Cl)Cl>[ClH:33].[ClH:33].[NH2:26][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[C:16]([CH:14]([OH:15])[CH2:13][O:12][CH2:11][CH2:10][N:8]([CH3:7])[CH3:9])=[CH:17][CH:18]=[CH:19]2

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21887872Ethanol hydrochlorideHCID 67596183HCID 67596183, compound

Product 1

HCID 67597753HCID 67597753, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 150 mg of 2-[2-(N,N-dimethyl-amino)ethoxy]-1-(8-nitro-1-naphthyl)ethanol oxalate, 150 mg of 5% palladium-carbon and 3 ml of methanol was subjected to hydrogenation at room temperature for 30 minutes under atmospheric pressure. After the completion of the reaction, the palladium-carbon was removed by filtration. The filtrate was subjected to distillation under reduced pressure to remove the solvent. The residue thus obtained was added to a mixture of 30 ml of ice water and 30 ml of chloroform. The mixture was adjusted to pH 11 with a 2N aqueous sodium hydroxide solution. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was dissolved in 1 ml of ethanol. Thereto was added 0.2 ml of a 5.9N dry hydrogen chloride-ethanol solution. The resulting crystals were collected by filtration and dried to obtain 110 mg of 1-(8-amino-1-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol dihydrochloride (compound No. 290).

Workup

  1. customAfter the completion of the reaction
  2. customthe palladium-carbon was removed by filtration
  3. distillationThe filtrate was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. customThe residue thus obtained
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. filtrationThe resulting crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-16d0b2b28d854a53b8a754ee571277aa
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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