Diethyl (ethoxymethylene)malonate → HCID 117601199, compound

HRID 526413Notes

Reaction equation

HRID 526413 reaction equation
Cl.[NH:2]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[O:9])=[CH:6][N:5]=1)[NH2:3].C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C.C(=O)([O-])[O-].[K+:37].[K+]>O.C(O)C>[CH2:26]([O:25][C:23]([C:22]1[CH:28]=[N:3][N:2]([C:4]2[CH:17]=[CH:16][C:7]([C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:6][N:5]=2)[C:21]=1[O-:20])=[O:24])[CH3:27].[K+:37]

Participants

6

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 117601529HCID 117601529, compound

Product 1

HCID 117601199HCID 117601199, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 6-hydrazinyl-N-(3-methoxypropyl)nicotinamide hydrochloride (7.5 g, 28.8 mmol), diethyl 2-(ethoxymethylene)malonate (14 mL, 69 mmol), and potassium carbonate (9.94 g, 71.9 mmol) in water (150 mL) and ethanol (25 mL) and stirred at 25° C. for 3 h and then at 60° C. for 18 h. The mixture was cooled to 20° C. to give a precipitate which was collected by filtration and washed with water to give the title compound (8.14 g, 73.2% yield) as a yellow solid. MS m/z 349 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (t, J=7.1 Hz, 3H) 1.77 (quin, J=6.7 Hz, 2H) 3.25 (s, 3H) 3.27-3.34 (m, 2H) 3.38 (t, J=6.3 Hz, 2H) 4.02 (q, J=7.1 Hz, 2H) 7.52 (s, 1H) 8.10 (dd, J=8.8, 2.5 Hz, 1H) 8.42 (dd, J=8.8, 0.5 Hz, 1H) 8.48 (t, J=5.6 Hz, 1H) 8.78 (dd, J=2.4, 0.6 Hz, 1H).

Workup

  1. waitat 60° C. for 18 h
  2. temperatureThe mixture was cooled to 20° C.
  3. customto give a precipitate which
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-e9658538d3064424b262fa35c1fc75b1
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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