6-[5-Cyano-2-hydroxy-1-(2-methylpropenyl)benzyl]pyrazine 1-oxide → 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrazine 1-oxide

HRID 1073956Notes

Reaction equation

HRID 1073956 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]([OH:21])[C:7](C=C(C)C)([CH:16]=1)[CH2:8][C:9]1[N+:14]([O-:15])=[CH:13][CH:12]=[N:11][CH:10]=1)#[N:2]>C(OCC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:21][C:3]([CH3:4])([CH3:16])[CH2:1][CH:8]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][N+:14]=3[O-:15])[C:7]=2[CH:16]=1)#[N:2]

Participants

3

Reactant 1

HCID 221569356-[5-Cyano-2-hydroxy-1-(2-methylpropenyl)benzyl]pyrazine 1-oxide

Product 1

HCID 198956162-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrazine 1-oxideYield 11.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In an analogous manner to that described in the first paragraph of Example 8, from 0.35 g of 6-[5-cyano-2-hydroxy-1-(2-methylpropenyl)benzyl]pyrazine 1-oxide there was obtained 0.02 g of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyrazine 1-oxide in the form of a white solid of melting point 166°-168° C. (from diethyl ether).

Sources & evidence

ORD record
ord-f9929dcb390647fa8036fbc73c9afeab
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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