Pyridine → HCID 18790158, compound

HRID 1107115Notes

Reaction equation

HRID 1107115 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:21][NH:22][O:23][CH3:24].N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH3:24][O:23][N:22]([CH3:21])[C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 16757Benzenepentanoic acidHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 18790158HCID 18790158, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2 g (11.22 mmol) of 5-phenylvaleric acid in 75 mL of CH2Cl2 at 0° C. under argon is added 2 drops of DMF followed by 7 mL (14.03 mmol) of oxalyl chloride. This stirred at 25° C. for 1 hour, then 1.4 g (14.03 mmol) of N,O-dimethylhydroxylamine hydrochloride and 2.7 mL (33.66 mmol, 3 eq) of pyridine are added sequentially and stirred for 72 hours at 25° C. The reaction is partitioned between CH2Cl2 and 1 N HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo to give 2.5 g (100%) of 5-phenylpentanoic acid-methoxy-methyl-amide in the form of a yellow oil.

Workup

  1. stirringstirred for 72 hours at 25° C
  2. customThe reaction is partitioned between CH2Cl2 and 1 N HCl
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02ac41c08119491381cfdec214f2cd90
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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