Hydrochloric Acid → 1-Methoxy-6-phenyl-6H-benzo[c]chromen-8-ylamine

HRID 1358117Notes

Reaction equation

HRID 1358117 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14]C)=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17]OC)=[C:4]([CH:20](O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=1.Cl>CO.O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([O:16][CH3:17])=[CH:10][CH:11]=[CH:12][C:13]=3[O:14][CH:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 181891954-Amino-2(alpha-hydroxybenzyl)-2'-methoxymethoxy-6'-methoxy-biphenyl

Product 1

HCID 181892091-Methoxy-6-phenyl-6H-benzo[c]chromen-8-ylamineYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

The compound of Example 5E (3.449 g., 9.45 mmole) was dissolved in methanol (80 mL) containing 4N HCl in dioxane (80 mL)was stirred for 16 hours. The mixture was concentrated under reduced pressure, dissolved in chloroform washed with aqueous KHCO3, dried (Na2SO4), filtered and reduced under pressure. The residue was dissolved in toluene (450 mL), toluenesulfonic acid H2O (7.18 g.) was added and the solution was heated at 85° C. for 30 minutes. The mixture was cooled, washed with aqueous KHCO3, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica eluting with CH2Cl2 to provide the titled compound (2.49 g, 87%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in chloroform
  3. washwashed with aqueous KHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. dissolutionThe residue was dissolved in toluene (450 mL)
  7. additiontoluenesulfonic acid H2O (7.18 g.) was added
  8. temperatureThe mixture was cooled
  9. washwashed with aqueous KHCO3
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified on silica eluting with CH2Cl2

Sources & evidence

ORD record
ord-00ac1940af364b04a3f0a4cc9b13b0c7
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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