4-tert-Butylpyridine → 8-Methylquinoline

HRID 1940881Notes

Reaction equation

HRID 1940881 reaction equation
C([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)(C)(C)C>C(O)C>[CH3:9][C:10]1[CH:5]=[CH:6][CH:7]=[C:10]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

3

Reactant 1

HCID 198784-tert-Butylpyridine

Product 1

HCID 119108-Methylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reactor effluent vapor was directed through a condenser and the recovered liquid was weighed at convenient times. Typically, the liquid obtained from the first 20 minutes of the run was discarded. Three one-hour test periods were then taken with the mid-point of each period representing 0.8, 1.8 and 2.8 hours-on-stream (HOS). The reaction crudes were homogenized with ethanol before adding 4-tert-butylpyridine as a standard. The samples were then analyzed by GC using standard techniques. The reported 8-methylquinoline selectivity and yield are based on the moles of ortho-toluidine. The purity of the 8-methylquinoline is based on the 8-methylquinoline/2,8-dimethylquinoline (2,8 -Me2Q) weight ratio.

Workup

  1. customThe reactor effluent vapor was directed through a condenser
  2. customTypically, the liquid obtained from the first 20 minutes of the run
  3. custom0.8, 1.8 and 2.8 hours
  4. customThe reaction crudes

Sources & evidence

ORD record
ord-edc38b60383745c4825b9fd1be99f9d5
Source dataset
uspto-grants-1997_12
Patent number
US05700942

Reaction notes

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