Diethyl (ethoxymethylene)malonate → HCID 178469984, compound

HRID 514336Notes

Reaction equation

HRID 514336 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=1)[NH2:2].[CH2:11]([O:13][C:14](=[O:25])[C:15](=[CH:21]OCC)[C:16](OCC)=[O:17])[CH3:12].C([O-])([O-])=O.[K+].[K+]>O>[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([N:1]2[C:16]([OH:17])=[C:15]([C:14]([O:13][CH2:11][CH3:12])=[O:25])[CH:21]=[N:2]2)[CH:8]=1)#[N:10]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 178469984HCID 178469984, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-hydrazinylpyridine-4-carbonitrile (5.36 g, 40 mmol, PREPARATION 2), diethyl(ethoxymethylidene)propanedioate (8.64 g, 40 mmol) and K2CO3 (10.76 g, 80 mmol) in H2O (100 mL) was stirred at 100° C. for 4 h. The reaction mixture was cooled to rt and filtered to afford the title compound (2.5 g, 24%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.19 (3H, t, J=7.2 Hz), 4.02 (2H, q, J=7.2 Hz), 7.38 (1H, dd, J=4.8, 1.6 Hz), 7.53 (1H, s), 8.53 (1H, d, J=5.2 Hz), 8.79 (1H, s). [M+H] Calc'd for C12H10N4O3, 259. Found, 259.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered

Sources & evidence

ORD record
ord-c664cde81e4241cc884925212c343db9
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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