Sodium Sulfite → HCID 59409002, compound

HRID 1894731Notes

Reaction equation

HRID 1894731 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH2:2]1.[Br:13]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:13][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([CH2:1][CH2:2][N:3]3[CH2:4][CH2:5][CH2:6]2)[CH:10]=1

Participants

7

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 120264Lilolidine

Product 1

HCID 59409002HCID 59409002, compoundYield 86.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (4.0 g, 25.2 mmol) in N,N-dimethylformamide (160 ml) cooled to −30° C. was treated with a solution of N-bromosuccinimide (4.5 g, 25.3 mmol) in N,N-dimethylformamide (30 ml) dropwise over 5 minutes. The mixture was stirred for a further 15 minutes then treated with 10% aqueous sodium sulfite (100 ml) then diluted with water (500 ml) and ethyl acetate (300 ml). The aqueous layer was removed and the organic layer was washed with saturated aqueous sodium bicarbonate (100 ml), then water (3×150 ml). The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness to give 8-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline as a pale brown oil (5.2 g) which was used without further purification. 400 MHz 1H NMR (CDCl3) δ: 7.02 (m, 1H), 6.94 (m, 1H), 3.25 (t, 2H), 2.95 (m, 2H), 2.89 (t, 2H), 2.65 (t, 2H), 2.06 (m, 2H); LCMS: 238 and 240 [M+H].

Workup

  1. customThe aqueous layer was removed
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate (100 ml)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6e17d5abfb774c40a56d23ac148fa066
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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