Hydrogen Bromide → HCID 86745037, compound

HRID 728234Notes

Reaction equation

HRID 728234 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[CH2:16][CH:15]4[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]4)[C:9]=3[C:8]=2[CH:22]=1.[BrH:23]>>[BrH:23].[CH3:21][N:17]1[CH2:16][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C@@H:9]2[C@@H:18]1[CH2:19][CH2:20][C:7]1[CH:6]=[CH:5][C:4]([OH:3])=[CH:22][C:8]=12

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 67945809HCID 67945809, compound

Product 1

HCID 86745037HCID 86745037, compound

Procedure

(See FIG. 2) A suspension of 0.456 g. (1.44 mmol) of 11-methoxy-6- methyl-hexahydrobenzo[a]phenanthridine hydrochloride in 10 ml 48% HBr was heated for 2.5 hours at reflux under N2 in an oil bath. The heat was removed, and the reaction mixture was placed in the refrigerator overnight. The white precipitate was collected by suction filtration, and after washing the crystals on the filter with cold ethanol and ether, the product weighed 403 mg (80.6%), mp 251°-254° C. The filtrate was concentrated and the residue was crystallized from ethanol to provide additional product, giving essentially a quantitative total yield of the phenol, mp 254° C. CIMS (NH3): M+1 266; 1H-NMR (CDCl3, free base); δ 7.38 (d, 1, ArH, J=7.5 Hz), 7.22 (m, 3, ArH), 7.04 (d, 1, ArH, J=8.2 Hz), 6.69 (s, 1, ArH); 6.64 (d, 1, ArH, J=8.2 Hz,) 3.98 (d, 1, Ar2CH), 3.84 (d, 1, ArCH2N, J=14.5 Hz), 3.50 (d, 1, ArCH2N, J=14.5 Hz), 2.87 (m, 2, CH2 and CHN) 2.38 (s, 3, NCH3), 2.09 (m, 2, CH), 1.86 (m, 1, CH2CN).

Workup

  1. addition(See FIG. 2) A suspension of 0.456 g
  2. temperatureat reflux under N2 in an oil bath
  3. customThe heat was removed
  4. customwas placed in the refrigerator overnight
  5. filtrationThe white precipitate was collected by suction filtration
  6. washafter washing the crystals on the
  7. filtrationfilter with cold ethanol and ether
  8. concentrationThe filtrate was concentrated
  9. customthe residue was crystallized from ethanol
  10. customto provide additional product

Sources & evidence

ORD record
ord-28d0155cf4d445b7a1f339acf706e83b
Source dataset
uspto-grants-1991_09
Patent number
US05047536

Reaction notes

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