Sulfuric Acid → 4-(2-Methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinecarboxamide

HRID 1182375Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.S(=O)(=O)(O)[OH:24].[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[C:11]([C:12]([NH2:13])=[O:24])=[CH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 80 °C

Procedure

480 mg (1.642 mmol) 6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinonitrile were treated with 3.8 ml sulfuric acid (90%) and heated at 80° C. for 1 hour. The mixture was cooled down to 20-25° C. and treated with 20 ml ethyl acetate. 2.0 g sodium hydroxide solution (28%) was added and the organic phase was washed with 6 ml water. Evaporation in vacuo gave 380 mg of 6-(4-methylpiperazin-1-yl)-4-o-tolyl-nicotinamide as a light yellow crystalline foam.

Workup

temperatureThe mixture was cooled down to 20-25° C.
washthe organic phase was washed with 6 ml water
customEvaporation in vacuo

Sources & evidence

ORD record: ord-2d2d21f91d3f48d48b4b462b34889876
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288658B2

Reaction notes

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