Acetic Anhydride → HCID 66700168, compound

HRID 1910717Notes

Reaction equation

HRID 1910717 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[NH:5][CH:4]([CH3:12])[CH2:3]1.C(N(CC)CC)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>ClCCl>[C:20]([N:5]1[C:6]2[C:11](=[CH:10][N:9]=[CH:8][CH:7]=2)[C:2](=[O:1])[CH2:3][CH:4]1[CH3:12])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66700199HCID 66700199, compound

Product 1

HCID 66700168HCID 66700168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

[Step 4] 30 mg of the 4-oxo-2-methyl-2,3-dihydro-1H-[1,6]naphthyridine were dissolved in 2 mL of dichloromethane followed by adding 0.1 mL of triethylamine and 35 μL of acetic anhydride and stirring overnight at 40° C. Following completion of the reaction, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate) to obtain 7 mg of 1-acetyl-4-oxo-2-methyl-2,3-dihydro-1H-[1,6]naphthyridine in the form of a pale yellow oil (18%).

Workup

  1. customcompletion of the reaction
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe resulting residue was purified

Sources & evidence

ORD record
ord-662b4ca3ffd549a9ba15a9390a748ae8
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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