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

HRID 892587
Notes
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Reaction equation

HRID 892587 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:21])=[C:7]([CH:20]=1)[CH:8]([C:13]1[N+:18]([O-:19])=[CH:17][CH:16]=[N:15][CH:14]=1)[CH:9]=[C:10]([CH3:12])[CH3:11])#[N:2]>C(OCC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:21][C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][N+:18]=3[O-:19])[C:7]=2[CH:20]=1)#[N:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 198955986-[5-Cyano-2-hydroxy-alpha-(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 5.7%

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-α-(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-e047655418ca41dd929c052f2421d6ff
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05118694

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes