Diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate → HCID 178469681, compound

HRID 2092334Notes

Reaction equation

HRID 2092334 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19]CC)=O)[C:9]2=[O:27])=[CH:5][CH:4]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[C:9](=[O:27])[C:10]3[N:14]=[CH:15][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([OH:19])[C:11]=3[CH:12]=[CH:13]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 67340511Diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate

Product 1

HCID 178469681HCID 178469681, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

Dowtherm A (50 ml) was heated to 250° C. in a 500 ml a 3-neck rbf equipped with a temperature probe, a stir bar and a reflux condenser. Diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate (5.00 g, 12.5 mmol) was added in one portion. The mixture was stirred for 30 mins and then was rapidly cooled down using a stream of nitrogen. At around 140° C., a solid started to crash out. Once at RT, the mixture was diluted with hexanes (100 ml) and was allowed to stand overnight. The precipitate that formed was collected by suction filtration, washed with ether and dried to give ethyl 7-(4-methoxybenzyl)-4-hydroxy-8-oxo-7,8-dihydro-1,7-naphthyridine-3-carboxylate as a yellow solid. MS(M+H)+ 355.

Workup

  1. customequipped with a temperature probe, a stir bar and a reflux condenser
  2. temperaturewas rapidly cooled down
  3. customAt around 140° C.
  4. waitto stand overnight
  5. customThe precipitate that formed
  6. filtrationwas collected by suction filtration
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-e70295d198704dc58bcfe322c06ca383
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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