Dimethyl malonate → HCID 135834128, compound

HRID 1017627Notes

Reaction equation

HRID 1017627 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5]C)=O.[Na].[C:11]1([N:17]2[C:21]([NH2:22])=[C:20]([CH:23]=O)[N:19]=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO.O>[C:11]1([N:17]2[C:21]3[NH:22][C:3](=[O:5])[C:2]([C:1]([O:8][CH3:9])=[O:7])=[CH:23][C:20]=3[N:19]=[N:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 125231665-Amino-1-phenyl-1H-1,2,3-triazole-4-carbaldehyde

Product 1

HCID 135834128HCID 135834128, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Dimethyl malonate (0.31 ml, 2.7 mmol) was added at room temperature to a stirred solution of sodium (0.065 g, 2.7 mmol) dissolved in dry methanol (8 ml) under nitrogen. A solution of 1-phenyl-4-formyl-5-amino-1,2,3-triazole (Bull. Soc. Chim. Belg., 1988, 97, 85-86) (0.50 g, 2.66 mmol) in dry methanol (4 ml) was added and the mixture was stirred for 18 h. The white suspension was diluted with water (50 ml) and the solids were collected and dissolved in dichloromethane-methanol (2:1, 100 ml). The solution was washed with aqueous citric acid (1 M, 50 ml), dried (Na2SO4), filtered and concentrated to give 3-phenyl-5-oxo-6-methoxycarbonyl-4H-1,2,3-triazolo[4,5-b]pyridine (0.353 g, 49%) as a white powder. δH (360 MHz; DMSO) 3.89 (3H, s), 7.56 (1H, t, J=7.5), 7.68 (2H, dd, J=7.5 and 7.5), 8.09 (2H, d, J=7.5), 8.92 (1H, s) and 12.67 (1H, br s); m/z (ES+) 271 (M+H+).

Workup

  1. customthe solids were collected
  2. dissolutiondissolved in dichloromethane-methanol (2:1, 100 ml)
  3. washThe solution was washed with aqueous citric acid (1 M, 50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eec17fbb505748beb8cc9ddea9c3a7ac
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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