3-Methylpyridine → 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1441127Notes

Reaction equation

HRID 1441127 reaction equation
C(O[CH:4](OCC)[CH:5]=[C:6]([CH3:8])[CH3:7])C.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)#[N:13].N1C=CC=C(C)C=1>CC1C=CC(C)=CC=1>[CH3:7][C:6]1([CH3:8])[CH:5]=[CH:4][C:16]2[CH:15]=[C:14]([C:12]#[N:13])[CH:19]=[CH:18][C:17]=2[O:20]1

Participants

5

Reactant 3

HCID 79703-MethylpyridineHCID 130194-CyanophenolHCID 52153201,1-Diethoxy-3-methyl-2-butene

Product 1

HCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A 500-mL, 3-necked, round-bottomed flask topped with a distilling head, internal temperature probe/argon inlet, and an overhead stirrer was sequentially charged with the title A compound, 1,1-diethoxy-3-methyl-2-butene (26.59 g, 168.00 mmol), p-xylene (300 mL), 4-cyanophenol (15.00 g, 125.92 mmol), and 3-picoline (3.0 mL, 2.870 g, 30.83 mmol). The reaction mixture was rapidly stirred. The internal temperature was rapidly brought up to 115° C. and then slowly raised in order to distill off the ethanol formed during the reaction.

Workup

  1. customA 500-mL, 3-necked, round-bottomed flask topped with a distilling head, internal temperature probe/argon inlet, and an overhead stirrer
  2. customwas rapidly brought up to 115° C.
  3. temperatureslowly raised in order
  4. distillationto distill off the ethanol
  5. customformed during the reaction

Sources & evidence

ORD record
ord-6307a561c5a2442185cf274898040c01
Source dataset
uspto-grants-1996_03
Patent number
US05502220

Reaction notes

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