N-[(4-chlorophenyl)methyl]-6-iodo-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide → N-[(4-chlorophenyl)methyl]-1-methyl-4,7-dioxo-8H-1,8-naphthyridine-3-carboxamide

HRID 2120775Notes

Reaction equation

HRID 2120775 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[N:14][C:15]([O:22]C)=[C:16](I)[CH:17]=3)[N:12]([CH3:24])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[CH:17]=[CH:16][C:15](=[O:22])[NH:14][C:13]=3[N:12]([CH3:24])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 5276330N-[(4-chlorophenyl)methyl]-6-iodo-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamideHCID 10176127Pyridinium chloride

Product 1

HCID 6320653N-[(4-chlorophenyl)methyl]-1-methyl-4,7-dioxo-8H-1,8-naphthyridine-3-carboxamideYield 56.3%

Conditions

Temperature
200 °C

Procedure

N-(4-Chlorobenzyl)-6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide (150 mg) is mixed with pyridine hydrochloride (1.50 g). The resulting solid is heated at 200° C. for 1 h, then cooled to room temperature and washed with MeOH. The residue is then dissolved in CH2Cl2, washed with 1N HCl, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product is purified by silica gel chromatography (CH2Cl2/MeOH 19/1, 9/1) to afford 60 mg (56%) of N-(4-chlorobenzyl)-1-methyl-4,7-dioxo-1,4,7,8-tetrahydro[1,8]naphthyridine-3-carboxamide. Physical characteristics are as follows: 1H NMR (DMSO-d6) δ8.85, 8.44, 7.42-7.33, 6.82, 4.55, 3.92; IR (diffuse reflectance) 3044, 2350, 2318, 1941, 1908, 1679, 1645, 1627, 1553, 1524, 1504, 1466, 803, 672, 656, cm−1.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with MeOH
  3. dissolutionThe residue is then dissolved in CH2Cl2
  4. washwashed with 1N HCl, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by silica gel chromatography (CH2Cl2/MeOH 19/1, 9/1)

Sources & evidence

ORD record
ord-d48c33b2a7454a4dbe8fd990e3d3fac3
Source dataset
uspto-grants-2004_02
Patent number
US06693114B2

Reaction notes

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