Pyrrolidine → HCID 11195876, compound

HRID 1006140Notes

Reaction equation

HRID 1006140 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][OH:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH3:14][C:4]1[CH:3]=[C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:11]2[C:6](=[CH:7][C:8]([CH2:12][OH:13])=[CH:9][CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 11264243HCID 11264243, compound

Product 1

HCID 11195876HCID 11195876, compoundYield 90%

Procedure

(4-Chloro-2-methyl-quinolin-7-yl)-methanol (750 mg, 3.61 mmol) was refluxed in pyrrolidine (6.42 g, 90.3 mmol) for 16 h. Most of the pyrrolidine was then removed under reduced pressure, the oily residue was taken up in toluene, evaporated, and the solid obtained triturated in ethyl acetate, filtered and dried to afford the title compound (785 mg, 90%). Light brown solid, ISP-MS: m/e==243.3 ([M+H]+).

Workup

  1. customMost of the pyrrolidine was then removed under reduced pressure
  2. customevaporated
  3. customthe solid obtained
  4. customtriturated in ethyl acetate
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-6485a9e0fac340e694eb7d77c44d772d
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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