Pyrrolidine-1-carbonitrile → HCID 178487758, compound

HRID 1852104Notes

Reaction equation

HRID 1852104 reaction equation
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1C)C.C([Li])(C)(C)C.[N:22]1(C#N)[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([OH:14])=[N:3][C:15]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:16]2

Participants

5

Reactant 3

HCID 73737Pyrrolidine-1-carbonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 178487758HCID 178487758, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (0.270 g, 1.220 mmol) in THF (10 mL) was added tert-butyllithium (1.077 mL, 1.830 mmol) dropwise at −78° C. After stirring for 0.5 h, pyrrolidine-1-carbonitrile (0.135 mL, 1.342 mmol) was added, then the solution was warmed to rt, and stirred for 16 h. The reaction mixture was quenched with MeOH, neutralized with 1.5 mL of 4.0M HCl in dioxane. Extracted product with 20 mL of DCM. The solution was evaporated on rotovap and then placed under high vacuum for 1 h to give 6-methoxy-3-(pyrrolidin-1-yl)isoquinolin-1-ol (298 mg, 100% yield) which was used in the next step without further purification. MS m/z 245.1 (M++1).

Workup

  1. stirringstirred for 16 h
  2. customThe reaction mixture was quenched with MeOH
  3. customThe solution was evaporated on rotovap
  4. waitplaced under high vacuum for 1 h

Sources & evidence

ORD record
ord-bfa5087cc40641a6a4d891c5540858e6
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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