Toluene → HCID 10154406, compound

HRID 1279231Notes

Reaction equation

HRID 1279231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]([NH2:20])=O)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22](N)([CH3:25])[CH2:23][NH2:24].C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:9])[C:18]3=[N:20][C:22]([CH3:25])([CH3:21])[CH2:23][N:24]3[C:10](=[O:17])[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][C:16]2=3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 131282-MethylpropylenediamineHCID 12017609HCID 12017609, compound

Product 1

HCID 10154406HCID 10154406, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(4-chlorobenzoyl)-2-pyridinecarboxylic acid (13 g), potassium cyanide (4.56 g), and acetic acid (30 mL) was heated at 120-125 C. in a sealed pressure bottle for 48 h. After cooling to ambient temperature, the mixture was poured into ice water. The precipitated solid was dissolved in ethyl acetate, washed with sodium bicarbonate saturated solution then with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was treated with ether. The formed solid was collected by filtration and dried to give 10.2 g of 5-(4-chlorophenyl)-7-oxo-5,7-dihydrofuro[3,4-b]pyridine-5-carboxamide. A mixture of 5-(4-chlorophenyl)-7-oxo-5,7-dihydrofuro[3,4-b]pyridine-5-carboxamide (5 g), 2-methyl-1,2-diamino propane (6.3 g), and toluene (80 mL) was heated at reflux for 18 h in a flask equipped with a water separator. The mixture was cooled to ambient temperature. The precipitated material was collected by filtration and dried to give the title compound (2.4 g), m.p. 257-260° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h in a flask
  3. filtrationThe precipitated material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-dcadc3624d474dada1c08d12c3a13e5b
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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