Isoquinoline, 1-chloro- → N-(3-Bromobenzoyl)-N-(1-isoquinolyl)hydrazine

HRID 574035

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([NH:18][NH2:19])=[O:17]>C1(C)C=CC(C)=CC=1>[Br:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([N:18]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)[NH2:19])=[O:17]

Participants

Conditions

Temperature: 150 °C

Procedure

To a 200-mL three-neck flask were added 3.3 g (20 mmol) of 1-chloroisoquinoline, 4.3 g (20 mmol) of 3-bromobenzoylhydrazine, and 80 mL of para-xylene. This mixture was refluxed at 150° C. for 14 hours under a nitrogen stream. After a predetermined time elapsed, this mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The obtained solid was washed with toluene, a saturated aqueous solution of sodium hydrogen carbonate, and water. This solid was dried, so that the substance which was the object of the synthesis was obtained as 6.2 g of a pale yellow powder in 90% yield.

Workup

temperaturethis mixture was cooled to room temperature
filtrationthe precipitated solid was collected by suction filtration
washThe obtained solid was washed with toluene
customThis solid was dried, so that the substance which

Sources & evidence

ORD record: ord-a111e756426347d48c5a10da0b2ef81a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034486B2

Linked notes

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