Chlorosuccinimide → 6-Chloro-1,2,3,4-tetrahydroquinoline

HRID 1815905Notes

Reaction equation

HRID 1815905 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 694601,2,3,4-Tetrahydroquinoline2×

Product 1

HCID 111828396-Chloro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Based on R. Nagata et al., J. Med. Chem., 1994, 37, 3956-3968, 1,2,3,4-tetrahydroquinoline (1.33 g, 10 mmol) was dissolved in DMF (15 mL) under N2 and cooled to 0° C. N-Chlorosuccinimide (1.35 g, 10 mmol) was dissolved in DMF (10 mL) under N2 and was added to the tetrahydroquinoline solution dropwise, via pressure equalizing dropping funnel, over 45 min. The reaction was stirred at 0° C. for 3 h, then quenched by pouring it into water (100 mL). This mixture was extracted with a 5:1 mixture of EtOAc:toluene, then two times with EtOAc. All of the organic extracts were washed with brine, combined, dried over Na2SO4, filtered, and concentrated, then eluted through a 17×2.5 cm column of silica gel (5%, 10% and 15% EtOAc/Hexane step gradient) giving 6-chloro-1,2,3,4-tetrahydroquinoline as a green oil.

Workup

  1. customquenched
  2. additionby pouring it into water (100 mL)
  3. extractionThis mixture was extracted with a 5:1 mixture of EtOAc
  4. washAll of the organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted through a 17×2.5 cm column of silica gel (5%, 10% and 15% EtOAc/Hexane step gradient)

Sources & evidence

ORD record
ord-46770f0dda49424b9b14007a408ce3de
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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