Diethyl Ether → 2,2-Dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile

HRID 1073935Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1.C([O:23]CC)C>>[C:18]([C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:20])([CH3:1])[CH2:7][CH:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=3[O-:23])[C:5]=2[CH:14]=1)#[N:19]

Participants

Reactant 2

HCID 3283Diethyl Ether

HCID 150389003,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 63363852,2-Dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile

Procedure

In an analogous manner to that described in the first paragraph of Example 7, from (-)-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile there was obtained (-)-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1 -benzopyran-4-yl)pyridine N-oxide of melting point 142°-144° C. (from diethyl ether); [α]58920 =76.8° (c=0.997 in ethanol).

Sources & evidence

ORD record: ord-d37bbb0748df4af287507b22f1497729
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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