Hydrochloric Acid → HCID 131716988, compound

HRID 2249109Notes

Reaction equation

HRID 2249109 reaction equation
Cl.[NH2:2][CH:3]1[CH:16]([OH:17])[CH:15]([Cl:18])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][C:5]=2[CH2:4]1.Cl>FC(F)(F)C(O)=O.CO.C(OCC)C>[ClH:18].[NH2:2][CH:3]1[C:16](=[O:17])[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][C:5]=2[CH2:4]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 19995570HCID 19995570, compound

Product 1

HCID 131716988HCID 131716988, compoundYield 52.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Amino-4-chloro-l,2,3,4-tetrahydro-3-phenanthrenol, hydrochloride (265 mg) was refluxed in trifluoroacetic acid (25 ml) for 3 hours. The green mixture was evaporated in vacuo, taken up into methanol and treated with activated charcoal for 2 hours at room temperature. Filtration and evaporation yielded a yellow oil which was diluted with methanol and acidified with a solution of hydrochloric acid in diethyl ether. The mixture was evaporated and the acidification process was repeated. Evaporation gave a residue which was recrystallized in a methanol/diethyl ether mixture to afford the title compound (122 mg) as a cream colored powder.

Workup

  1. customThe green mixture was evaporated in vacuo
  2. additiontreated with activated charcoal for 2 hours at room temperature
  3. filtrationFiltration and evaporation
  4. customyielded a yellow oil which
  5. customThe mixture was evaporated
  6. customEvaporation
  7. customgave a residue which
  8. customwas recrystallized in a methanol/diethyl ether mixture

Sources & evidence

ORD record
ord-a6606688c5574d9ab120edf166e40917
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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