Hydrochloric Acid → HCID 13655877, compound

HRID 330244Notes

Reaction equation

HRID 330244 reaction equation
[OH:1][C:2]1[C:3]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH2:16])=[CH:4][C:5]([CH3:13])=[C:6]2[C:10]=1[C:9](=[N:11]O)[CH2:8][CH2:7]2.[H][H].[ClH:25]>C(O)(=O)C.C(O)C.[Pt]=O>[ClH:25].[NH2:11][CH:9]1[C:10]2[C:6](=[C:5]([CH3:13])[CH:4]=[C:3]([CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH3:16])[C:2]=2[OH:1])[CH2:7][CH2:8]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 136342831HCID 136342831, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13655877HCID 13655877, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

2.93 Grams of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one oxime and 0.293 g of platinum oxide were suspended in 200 ml of acetic acid, then the suspension was reduced at room temperature under 3 atmospheric hydrogen pressure for 8 hours. After the completion of hydrogenation, the catalyst was removed by filtration, and the filtrate thus obtain was concentrated to dryness under a reduced pressure. The residue thus obtained was dissolved in 100 ml of ethanol and the pH of the solution was adjusted to about pH=1 by adding an ethanol solution saturated with hydrogen chloride gas, then this solution was again concentrated to dryness under a reduced pressure. The residue thus obtained was recrystallized from ethanoldiethyl ether to obtain 0.88 g of 1-amino-2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenylpropyl)-1H-indene hydrochloride. Colorless powdery crystals. Melting point: 187.5°-189.5° C.

Workup

  1. customAfter the completion of hydrogenation, the catalyst was removed by filtration
  2. customthe filtrate thus obtain
  3. concentrationwas concentrated to dryness under a reduced pressure
  4. customThe residue thus obtained
  5. concentrationthis solution was again concentrated to dryness under a reduced pressure
  6. customThe residue thus obtained
  7. customwas recrystallized from ethanoldiethyl ether

Sources & evidence

ORD record
ord-9266df9aa8af4097b35ff668c4575183
Source dataset
uspto-grants-1990_01
Patent number
US04895847

Reaction notes

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