Triethylamine → HCID 178513334, compound

HRID 1842031Notes

Reaction equation

[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:14][CH2:13][CH2:12]3)=[CH:5][CH:4]=1.Cl.[NH2:30][OH:31].C(N(CC)CC)C>O1CCCC1.CO>[OH:31][NH:30][C:23](=[NH:24])[C:22]1[CH:21]=[CH:20][C:19]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:28])([F:1])[F:27])=[CH:4][CH:5]=4)=[CH:18][CH:17]=3)[CH2:12][CH2:13][CH2:14]2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

305 mg 4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzonitrile were dissolved in a mixture of 10 ml tetrahydrofuran and 10 ml methanol. 1.19 g hydroxylamine hydrochloride were added followed by the addition of 2.42 ml triethylamine. The reaction mixture was stirred at 90° C. for four hours. The solvents were removed in vacuo and the resulting residue poured into 50 ml water and extracted five times with portions of 50 ml ethylacetate. The combined organic extracts were washed with 100 ml brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 355 mg crude N-Hydroxy-4-[6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzamidine. This material was used without further purification.

Workup

customThe solvents were removed in vacuo
additionthe resulting residue poured into 50 ml water
extractionextracted five times with portions of 50 ml ethylacetate
washThe combined organic extracts were washed with 100 ml brine
dry with materialdried over MgSO4
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-f51669681b0942b2a5361ef8e2db2066
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946212B2

Reaction notes

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