Pyrrolidine → HCID 91995409, compound

HRID 916326Notes

Reaction equation

HRID 916326 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[C:10]([N+:20]([O-:22])=[O:21])=[CH:9][CH:8]=1>>[ClH:6].[N+:17]([C:15]1[C:16]2[C:11](=[C:10]([N+:20]([O-:22])=[O:21])[CH:9]=[CH:8][CH:7]=2)[C:12]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:13][CH:14]=1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 2945164-Chloro-1,5-dinitronaphthalene

Product 1

HCID 91995409HCID 91995409, compoundYield 21%

Procedure

Pyrrolidine (5.0 mL) was added to 1-chloro-4,8-dinitronaphthalene (50 mg, 0.20 mmol, Bassilios et al, Recueil, 1962, 81, 209-214) which resulted in an immediate, highly exothermic reaction. The reaction was further agitated for 5 min while heating using a heatgun. Volatiles were removed in vacuo and purification as in 159JP06 (dichloromethane/n-heptane 4:1, 5× eluted) afforded 12 mg (21%) of 159JP29 as an orange solid. The product was converted to the corresponding hydrochloride salt as described above.

Workup

  1. customresulted in an immediate,
  2. customhighly exothermic reaction
  3. temperaturewhile heating
  4. customVolatiles were removed in vacuo and purification as in 159JP06 (dichloromethane/n-heptane 4:1, 5× eluted)

Sources & evidence

ORD record
ord-f4f01c956042408bae23a8838655ad30
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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