Isoniazid → 3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole

HRID 2102293

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.[C:7]([NH:15][NH2:16])(=O)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>C(Cl)Cl>[N:11]1[CH:12]=[CH:13][C:8]([C:7]2[N:1]3[CH2:5][CH2:4][CH2:3][C:2]3=[N:16][N:15]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Me3OBF4 (2.66 g, 18 mmol) was added to a solution of 2-pyrollidinone in DCM (150 ml) and the reaction mixture was stirred for 24 h. The reaction mixture was washed with aq. sat. NaHCO3, dried and concentrated. The residue was dissolved in EtOH (4 ml) and isonicotinic hydrazide (1.37 g, 10 mmol) was added. The mixture was heated in a microwave reactor for 1 h at 120° C. The volatiles were removed and the crude product purified with column chromatography (DCM/MeOH 20:1) to give 319 mg (11%) of the title compound. 1H NMR: 2.87 (m, 2H), 3.05 (t, 2H), 4.28 (t, 2H), 7.72 (d,2H), 8.72 (d, 2H).

Workup

washThe reaction mixture was washed with aq. sat. NaHCO3
customdried
concentrationconcentrated
dissolutionThe residue was dissolved in EtOH (4 ml)
customThe volatiles were removed
customthe crude product purified with column chromatography (DCM/MeOH 20:1)

Sources & evidence

ORD record: ord-abaf5ea9dffc43dba276908e4574fe5c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576077B2

Linked notes

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