N-Iodosuccinimide → 5-Iodo-2-methyl-1,7-naphthyridin-8(7H)-one

HRID 1787658Notes

Reaction equation

HRID 1787658 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:12])[C:4]=2[N:3]=1.[I:13]N1C(=O)CCC1=O>C(#N)C>[I:13][C:8]1[C:9]2[CH:10]=[CH:11][C:2]([CH3:1])=[N:3][C:4]=2[C:5](=[O:12])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 22090499HCID 22090499, compound

Product 1

HCID 686207215-Iodo-2-methyl-1,7-naphthyridin-8(7H)-oneYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methyl-7H-[1,7]naphthyridin-8-one (10.0 g, 62.4 mmol) was suspended in 300 ml acetonitrile and N-iodosuccinimide (16.9 g, 74.9 mmol) was added. The suspension was stirred for 3 hours at reflux. The reaction mixture was cooled to room temperature and filtered. The solid was washed with acetonitrile and dried for 30 minutes at 50° C. and <20 mbar, to get the desired compound as a brown solid (14.3 g, 80%), MS: m/e=287.0 (M+H+).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. washThe solid was washed with acetonitrile
  4. customdried for 30 minutes at 50° C.

Sources & evidence

ORD record
ord-6b8d0b48d52746f0ac11612a6701e8e3
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

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