Hydrogen Bromide → HCID 66673860, compound

HRID 423945Notes

Reaction equation

HRID 423945 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13]C)[CH:11]=2)[CH2:6][CH:5]2[NH:15][CH:4]12)[CH3:2].[BrH:18].C(OCC)(=O)C>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(O)C>[BrH:18].[NH2:15][CH:4]1[C:3]([CH2:16][CH3:17])([CH2:1][CH3:2])[C:12]2[CH:11]=[C:10]([OH:13])[CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]1[Br:18]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 159230752,2-Diethyl-4-methoxy-1a,2,7,7a-tetrahydro-1H-naphtho[2,3-b]azirene

Product 1

HCID 66673860HCID 66673860, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a flask was added 7,7-diethyl-5-methoxy-1a,2,7,7a-tetrahydro-1H-1-aza-cyclopropa[b]naphthalene (268 g, 1.16 mol) and hydrogen bromide (1.97 L, 17.38 mol), followed by tetra-N-butylammonium bromide (38 g, 0.12 mol). The reaction mixture was heated at 100° C. overnight with stirring, cooled to room temperature and then poured into stirred ethyl acetate (2.5 L). The product was isolated by filtration, the filter cake was washed with ethyl acetate (2×200 mL) and dried to yield crude product (370 g) as a purplish solid. The crude product was suspended in ethanol (1.50 L) then heated at 80° C. for 30 min. The resulting slurry was cooled to room temperature over 1 h, and filtered. The flask and filter cake with were washed with ethanol (2×100 mL) and then with ethyl acetate (100 mL) and dried overnight to yield the title compound (275 g, ˜96% purity).

Workup

  1. temperaturecooled to room temperature
  2. additionpoured
  3. customThe product was isolated by filtration
  4. washthe filter cake was washed with ethyl acetate (2×200 mL)
  5. customdried
  6. customto yield crude product (370 g) as a purplish solid
  7. temperaturethen heated at 80° C. for 30 min
  8. temperatureThe resulting slurry was cooled to room temperature over 1 h
  9. filtrationfiltered
  10. filtrationThe flask and filter cake
  11. washwith were washed with ethanol (2×100 mL)
  12. dry with materialwith ethyl acetate (100 mL) and dried overnight

Sources & evidence

ORD record
ord-9fe1c8757e4745a99ebc8c53adc17df4
Source dataset
uspto-grants-2012_01
Patent number
US08101794B2

Reaction notes

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