Tin tetrachloride → 1-(4-Amino-2-methylquinolin-3-yl)ethanone

HRID 1250452Notes

Reaction equation

[Sn](Cl)(Cl)(Cl)Cl.[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10].[C:15]([CH2:18][C:19](=O)[CH3:20])(=[O:17])[CH3:16]>>[NH2:10][C:9]1[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=[C:19]([CH3:20])[C:18]=1[C:15](=[O:17])[CH3:16]

Participants

Reactant 3

HCID 24287Tin tetrachloride

HCID 31261Acetylacetone

HCID 729132-Aminobenzonitrile

Product 1

HCID 6722971-(4-Amino-2-methylquinolin-3-yl)ethanone

Procedure

1-(4-Amino-2-methylquinolin-3-yl)ethanone was prepared analogously to Intermediate 2a, Example 6, by tin tetrachloride-promoted reaction of 2-aminobenzonitrile and acetyl acetone in a manner known from the literature (Tetrahedron 51:12277 (1995)).

Sources & evidence

ORD record: ord-021fc2a1c9a946dcaba3251d60e9b209
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339077B1

Reaction notes

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