Methyl iodide → ethyl 1-(N-formylmethylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 462695Notes

Reaction equation

HRID 462695 reaction equation
[CH:1]([NH:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]1)=O.[C:21](=O)([O-])[O-:22].[K+].[K+].CI>CN(C)C=O>[CH:21]([CH2:1][NH:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]1)=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13457703Ethyl 1-(formylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 20397058ethyl 1-(N-formylmethylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 1-(formylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate (11.8 g, 0.043 m) was added to a stirred mixture of 20.3 g (0.136 m) of anhydrous, milled potassium carbonate and 103 ml of dimethylformamide. The mixture was stirred for 30 minutes, and 20.3 ml (0.33 m) of methyl iodide was then added. The reaction mixture was stirred for five hours on a steam bath, then at room temperature overnight, and poured into 400 ml of ice-water. The solid product was collected by filtration, washed with water, and dried at 60° C. in vacuo to give 8.1 g of ethyl 1-(N-formylmethylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate, beige solid, m.p. 210°-212° C.

Workup

  1. stirringThe reaction mixture was stirred for five hours on a steam bath
  2. filtrationThe solid product was collected by filtration
  3. washwashed with water
  4. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-d16617708ed943e8a74a67fab6149cde
Source dataset
uspto-grants-1985_05
Patent number
US04517191

Reaction notes

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