6-Chloropyridazine-3-carbonitrile → 6-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

Reaction equation

Cl.[CH2:2]([NH:4][CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[OH:13])[CH3:3].Cl[C:15]1[N:16]=[N:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=1>>[Br:12][C:10]1[CH:9]=[CH:8][C:7]([OH:13])=[C:6]([CH:11]=1)[CH2:5][N:4]([C:15]1[N:16]=[N:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 133828716-Chloropyridazine-3-carbonitrile

HCID 22622504N-ethyl-5-bromo-2-hydroxybenzylamine hydrochloride

Product 1

HCID 226225146-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazineYield 50%

Procedure

The title compound was prepared by reacting N-ethyl-5-bromo-2-hydroxybenzylamine hydrochloride and 3-chloro-6-cyanopyridazine using a similar method to that of reference example 18 except eluting with 2% diethyl ether/dichloromethane in the chromatography (yield 50%).

Workup

washexcept eluting with 2% diethyl ether/dichloromethane in the chromatography (yield 50%)

Sources & evidence

ORD record: ord-01def716fe8e4d1dbf543ef9f28ef803
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365603B1

Reaction notes

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