Pyrrolidine → HCID 22054545, compound

HRID 1006149Notes

Reaction equation

HRID 1006149 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-565279a636284ae598b78c6b1afdf487
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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