Chlorosuccinimide → 5-Chloro-6-ethoxy-1,7-naphthyridin-8-amine

HRID 1881766Notes

Reaction equation

HRID 1881766 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[N:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[Cl:15]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:15][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[N:13][C:12]([NH2:14])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 130013416-Ethoxy-1,7-naphthyridin-8-amine

Product 1

HCID 687025425-Chloro-6-ethoxy-1,7-naphthyridin-8-amineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 200 mL round bottom flask was added 6-ethoxy-1,7-naphthyridin-8-amine (3.42 mmol), DCM (75 mL), followed by N-chlorosuccinimide (3.77 mmol). The mixture was heated at reflux for 18 h under Ar. The mixture was then cooled, the solvent evaporated and the resultant crude residue purified by silica gel to yield 5-chloro-6-ethoxy-1,7-naphthyridin-8-amine (480 mg, 63%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.89 (d, J=3.95 Hz, 1H), 8.43 (d, J=8.79 Hz, 1H), 7.66 (dd, J=8.79, 3.95 Hz, 1H), 4.13 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h under Ar
  3. temperatureThe mixture was then cooled
  4. customthe solvent evaporated
  5. customthe resultant crude residue purified by silica gel

Sources & evidence

ORD record
ord-d5e006dd13994ffda00efbd7cb9b22d1
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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