Sulfuric Acid → HCID 53936706, compound

HRID 1073909Notes

Reaction equation

HRID 1073909 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:22])=[C:7]([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N+:15]=2[O-:21])[CH:10]=[C:11]([CH3:13])[CH3:12])[CH:8]=1)#[N:2].S(=O)(=O)(O)O>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:22][C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N+:15]=3[O-:21])[C:7]=2[CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 53874904HCID 53874904, compound

Product 1

HCID 53936706HCID 53936706, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

350 mg of 2-[1-(5-cyano-2-hydroxyphenyl)-3-methyl-2-butenyl]-6-methylpyridine N-oxide in 15 ml of dichloromethane were stirred with 100 μl of concentrated sulphuric acid for 1 hour. A further 100 μl of concentrated sulphuric acid were added and stirring was continued for 30 minutes. The mixture was washed with water, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate (1:9) for the elution to give an oil which crystallized from diethyl ether. There was obtained 0.26 g of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-6-methylpyridine N-oxide of melting point 165°-167° C.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customto give an oil which
  7. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-91591430cd5a41c889bbc6481047a01a
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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