4-Methylpyridine → HCID 135504078, compound

HRID 2119313Notes

Reaction equation

HRID 2119313 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1>C(O)C>[OH:10][C:9]1[C:4]2[C:5](=[CH:11][CH:12]=[C:2]([CH3:1])[CH:3]=2)[C:6](=[O:8])[C:19]=1[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 880694-Methylphthalic anhydride

Product 1

HCID 135504078HCID 135504078, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 47.5 g (293 mmol) 4-methyl-phthalic anhydride and 28.6 ml (293 mmol) 4-pi-coline is heated to 165° C. for 18 h. The resulting material is stirred in 190 ml of boiling ethanol, filtered and washed with ethanol and diethyl ether, yielding the title compound: An. calc. (C15H11NO2) C, 75.94%; H, 4.67%; N, 5.90%; O, 13.49%; An. meas. C, 75.60%; H, 4.64%; N, 6.02%; O, 13.60%; 1H NMR (DMSO-d6) δ8.70 (d, 2H), 8.14 (d, 2H), 7.34 (m, 2H), 7.29 (s, 1H), 2.38 (s, 3H); FAB MS (M+H)+=238.

Workup

  1. filtrationfiltered
  2. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-4a433d1d06574b898870fd83c6f64dbd
Source dataset
uspto-grants-2004_02
Patent number
US06686347B2

Reaction notes

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