Pyrrolidine → HCID 23434005, compound

HRID 2121645Notes

Reaction equation

HRID 2121645 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9](F)[CH:10]=2)[N:5]=[C:4]([CH3:16])[CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH3:16][C:4]1[CH:3]=[C:2]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 23434001HCID 23434001, compound

Product 1

HCID 23434005HCID 23434005, compoundYield 86.1%

Procedure

A solution of 0.29 g (1.21 mmol) of 4-chloro-6-fluoro-2-methyl-7-nitro-quinoline in pyrrolidine (2 ml, 24 mmol) was heated at 80° C. (bath temperature) for 18 h. The excess pyrrolidine was removed in vacuo, the residue taken up in methylene chloride, which was washed with water, brine and then dried over magnesium sulfate. The solvent was removed in vacuo to give 0.34 g (79%) of the desired 2-methyl-7-nitro-4,6-di-pyrrolidin-1-yl-quinoline as dark red solid. ISP mass spectrum, m/e: 327.3 (M+1 calculated for C18H22N4O2: 327).

Workup

  1. customThe excess pyrrolidine was removed in vacuo
  2. washwhich was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bca29978fe5d44f9b4dfa22b8cf138c5
Source dataset
uspto-grants-2004_02
Patent number
US06696467B2

Reaction notes

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