Methanol → HCID 20529926, compound

HRID 261449Notes

Reaction equation

HRID 261449 reaction equation
B(Br)(Br)[Br:2].CO.C([N:9]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[C:23]([O:31]C)[C:24]([O:29]C)=[C:25]([CH2:26][CH2:27][CH3:28])[C:12]=2[CH2:11][CH2:10]1)=O>C(Cl)Cl.O>[BrH:2].[OH:29][C:24]1[C:23]([OH:31])=[CH:22][C:13]2[CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:15][NH:9][CH2:10][CH2:11][C:12]=2[C:25]=1[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15575015HCID 15575015, compound

Product 1

HCID 20529926HCID 20529926, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

This material (1.9 g, 0.0054 mole) in 50 ml of ethanol and 10 ml of 40% sodium hydroxide was heated at reflux for 2 hours. After stripping, the residue was taken up in methylene chloride-water. The combined organic layers were dried and evaporated to give the 7,8-dimethoxy compound which (1 g) was reacted with 1 ml of boron tribromide in dry methylene chloride for 3 hours. After stripping and cooling the residue was treated with methanol. The methanol was taken off and the residue dissolved in hot water (20 ml). Evaporation and cooling gave the dopaminergic agent 7,8-dihydroxy-6-n-propyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. 226°-229° (dec.).

Workup

  1. temperaturecooling the residue
  2. customEvaporation
  3. temperaturecooling

Sources & evidence

ORD record
ord-9a8ff1e4946a466f9212f79df6ceb8ee
Source dataset
uspto-grants-1979_08
Patent number
US04165372

Reaction notes

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