Acetic Acid → Ethyl 1-(formylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
Reaction equation
[C:1](O)(=[O:3])C.[NH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[C:9](=[O:17])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]1>C(O)=O>[CH:1]([NH:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[C:9](=[O:17])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]1)=[O:3]Participants
Procedure
Formic acid (13 ml, 0.33 m) was added to 31.2 ml (0.33 m) of acetic acid stirred in an ice bath. The mixture was stirred 15 minutes at 0° C. and 15 minutes at 55° C. It was then recooled to 0° C. and 8.1 g (0.033 m) of ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate was added. An additional 9.2 ml of formic acid was then added, and the reaction mixture was stirred one hour at 0° C. and two hours at room temperature. The reaction mixture was poured into ice-water, and the solid product collected by filtration, washed with water, tetrahydrofuran and ether, and dried at 75° C. in vacuo to give 4.4 g of ethyl 1-(formylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate, m.p. 214° C. (decompn), which contained a minor amount of the corresponding N,N-diformyl compound.
Workup
- stirringThe mixture was stirred 15 minutes at 0° C. and 15 minutes at 55° C
- customwas then recooled to 0° C.
- stirringthe reaction mixture was stirred one hour at 0° C. and two hours at room temperature
- filtrationthe solid product collected by filtration
- washwashed with water, tetrahydrofuran and ether
- customdried at 75° C. in vacuo
Sources & evidence
- ORD record
- ord-26ab32037d414fa6b0a5851ece5dca6a
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04517191
Reaction notes
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