Hydrogen Bromide → HCID 67823332, compound

HRID 2352318Notes

Reaction equation

HRID 2352318 reaction equation
Cl.C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C@H:10]([NH:15][CH2:16][CH2:17][CH3:18])[C@@H:11]2[CH3:14])=[CH:6][CH:5]=1.C(O)C.C(OCC)C.[BrH:27]>>[BrH:27].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C@H:10]([NH:15][CH2:16][CH2:17][CH3:18])[C@@H:11]2[CH3:14])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 702EthanolHCID 3283Diethyl EtherHCID 13900439HCID 13900439, compound

Product 1

HCID 67823332HCID 67823332, compoundYield 70%

Procedure

cis-7-Methoxy-1-methyl-2-(n-propylamino) tetralin hydrochloride (100 mg, 0.37 mmol) was heated in 48% aqueous HBr for 3 h at 120° C. under N2. The volatiles were evaporated from the faint pink solution and the residue was treated twice with ethanol followed by evaporation, giving a faint pink residue which was dissolved in abs. ethanol. Dry abs. ethyl ether was added to the solution, yielding white crystals which were then recrystallized from MeOH-ethyl ether, yielding the desired product (75 mg, 70% yield), m.p. 262°-263° C.

Workup

  1. customThe volatiles were evaporated from the faint pink solution
  2. additionthe residue was treated twice with ethanol
  3. customfollowed by evaporation
  4. customgiving a faint pink residue which
  5. dissolutionwas dissolved in abs
  6. customyielding white crystals which
  7. customwere then recrystallized from MeOH-ethyl ether

Sources & evidence

ORD record
ord-ee35158117cd4df785449615576f1f99
Source dataset
uspto-grants-1989_10
Patent number
US04876284

Reaction notes

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