Pyridine → HCID 60630334, compound

HRID 2200194Notes

Reaction equation

HRID 2200194 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].CCOC(C)=O>C1COCC1>[Cl:10][C:4]1[CH:3]=[C:2]([NH:1][C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 887284-Amino-2-chlorobenzonitrile

Product 1

HCID 60630334HCID 60630334, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-amino-2-chloro-benzonitrile (500 mg, 3.3 mmol) and pyridine (518 mg, 6.6 mmol) in THF (5 mL), cool to 0° C. and add slowly phenyl chloroformate (616 mg, 3.9 mmol). After addition, stir the reaction at room temperature for 2 hrs. TLC (EtOAc:PE=1:3) shows the reaction is complete. Add water, extract with DCM, separate the organic layer. Wash the organic layer with 1M HCl solution, brine sequentially, dry over anhydrous Na2SO4, and concentrate under reduced pressure to give the target compound (820 mg, 91.7%). MS: (M+1): 273.

Workup

  1. additionAfter addition
  2. customthe reaction at room temperature for 2 hrs
  3. extractionAdd water, extract with DCM
  4. customseparate the organic layer
  5. washWash the organic layer with 1M HCl solution, brine sequentially
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-cb38a28c641247d189b9dd20afc1e933
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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