Tin tetrachloride → HCID 68911690, compound

HRID 870361Notes

Reaction equation

HRID 870361 reaction equation
[CH2:1]([N:4]1[C@@H:13]2[C@H:8]([C:9]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[Sn](Cl)(Cl)(Cl)Cl>CO>[CH2:1]([N:4]1[C@@H:13]2[C@H:8]([C:9]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 68912516HCID 68912516, compound

Product 1

HCID 68911690HCID 68911690, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4aS,10bS)-4-Allyl-8-nitro-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline (0.85 g, 3.12 mmol) was dissolved in MeOH (50 mL) and tin chloride (3.50 g, 15.5 mmol) added. The solution was heated to reflux for 3 h and then evaporated. The residue was partitioned between ethyl acetate and NaOH (2M), and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and separated by preparative HPLC (20-90% MeOH) to give the 3 amino isomers. The product was obtained as a yellow oil (0.35 g, 46%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and NaOH (2M)
  5. customthe organic phase separated
  6. dry with materialdried over MgSO4
  7. concentrationThe filtered solution was concentrated
  8. customseparated by preparative HPLC (20-90% MeOH)
  9. customto give the 3 amino isomers

Sources & evidence

ORD record
ord-11f08c96bc874f0fa2356bd4044518fd
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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