2-Pyrrolidone → HCID 66877664, compound

HRID 1865569Notes

Reaction equation

HRID 1865569 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].ClC1C=CC(F)=C(C=1)C#N.N1CCCC1=O.[H-].[Na+]>CN(C=O)C>[Cl:9][C:7]1[CH:6]=[CH:5][C:4]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[C:3]([CH:8]=1)[C:2]#[N:1]

Participants

6

Reactant 4

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 936535-Chloro-2-fluorobenzonitrileHCID 668776451-(2-Aminomethyl-4-chloro-phenyl)-pyrrolidin-2-one

Product 1

HCID 66877664HCID 66877664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Aminomethyl-4-chloro-phenyl)-pyrrolidin-2-one: To 5-chloro-2-fluorobenzonitrile (0.3 g, 1.929 mmol) and pyrrolidin-2-one (0.246 g, 2.89 mmol) in DMF (5 mL) was added NaH (0.116 g, 2.89 mmol) and the reaction was stirred overnight. The reaction mixture was partitioned with EtOAc/water/brine and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and evaporated to give 5-Chloro-2-(2-oxo-pyrrolidin-1-yl)-benzonitrile (0.42 g). LCMS m/z 221.2 (M+H)+. This intermediate was converted to 125A following the procedure described for 102B. LCMS m/z 207.2 (M+H—NH3)+. 1HNMR (400 MHz, CHLOROFORM-D) δ: 2.08-2.20 (m, 2H) 2.57 (t, J=7.71 Hz, 2H) 3.56 (t, J=6.69 Hz, 2H) 4.61 (s, 2H) 6.50 (d, J=8.34 Hz, 1H) 6.97 (d, J=2.27 Hz, 1H) 7.11 (dd, J=8.34, 2.27 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned with EtOAc/water/brine
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2268726375bb4a478e8104d50c7e5d27
Source dataset
uspto-grants-2009_12
Patent number
US07626039B2

Reaction notes

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