Pyrrolidine → HCID 22054545, compound

HRID 1829749Notes

Reaction equation

HRID 1829749 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]([C:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])=[CH:9][CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 11264243HCID 11264243, compound

Product 1

HCID 22054545HCID 22054545, compoundYield 54%

Procedure

(4-Chloro-2-methyl-quinolin-7-yl)-methanol (example 2, 200 mg, 0.80 mmol) was heated in pyrrolidine (2 mL) at 70° C. for 48 h. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was separated, dried (MgSO4), and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 19:1) afforded the title compound (134 mg, 54%). Light yellow solid, ISP-MS: m/e=310.3 ([M+H]+).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7068a8d2857846d68a0309b0a18f4c90
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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