Pyrrolidine → HCID 57421475, compound

HRID 601509Notes

Reaction equation

HRID 601509 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CCOCC>[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:1](=[O:5])[C:2]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:3])=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 785026-Nitro-1H-indole

Product 1

HCID 57421475HCID 57421475, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add oxalyl chloride (11.6 g, 90.6 mmol) dropwise to a solution of 6-nitroindole (10.6 g, 65.4 mmol) in ether (100 mL). Stir at room temperature for 18 h, filter the precipitate formed, and dry. Dissolve the precipitate in CH2Cl2 (100 mL), cool to −20° C., and add pyrrolidine (16.0 mL, 191.5 mmol) dropwise. Warm to room temperature and stir for 2 h. Filter the solid from the reaction, wash several times with ether, and dry to give the title compound (8.5 g, 45%). MS (ES+) 288 (M+1)+.

Workup

  1. filtrationfilter the precipitate
  2. customformed
  3. customdry
  4. dissolutionDissolve the precipitate in CH2Cl2 (100 mL)
  5. temperaturecool to −20° C.
  6. temperatureWarm to room temperature
  7. stirringstir for 2 h
  8. filtrationFilter the solid
  9. customfrom the reaction
  10. washwash several times with ether
  11. customdry

Sources & evidence

ORD record
ord-a0cacadf72f64ae9aab291d6d4ba6abd
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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