HCID 19995552, compound → HCID 131716990, compound

HRID 2249116Notes

Reaction equation

HRID 2249116 reaction equation
[NH2:1][CH:2]1[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[CH:4]([Cl:16])[CH:3]1[OH:17]>FC(F)(F)C(O)=O>[ClH:16].[NH2:1][C@H:2]1[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[C@H:4]([Cl:16])[C@H:3]1[OH:17]

Participants

3

Reactant 1

HCID 19995552HCID 19995552, compound

Product 1

HCID 131716990HCID 131716990, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Amino-1-chloro-1,2,3,4-tetrahydro-2-phenanthrenol (103 mg) in trifluoroacetic acid (10 ml) was refluxed for 3 hours. The green mixture was evaporated and the residue was taken up in methanol and acidified with a solution of hydrochloric acid in diethyl ether. The evaporation residue was treated with charcoal in methanol. Filtration gave a clear solution which was evaporated to yield the crude compound as a solid (99 mg). Recrystallization from ethanol/diethyl ether afforded the title compound (40 mg) as a white solid, m.p. 247° C. (dec.).

Workup

  1. customThe green mixture was evaporated
  2. additionThe evaporation residue was treated with charcoal in methanol
  3. filtrationFiltration
  4. customgave a clear solution which
  5. customwas evaporated
  6. customto yield the crude compound as a solid (99 mg)
  7. customRecrystallization from ethanol/diethyl ether

Sources & evidence

ORD record
ord-2710bde68fbb496486622f59083c4879
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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