4-Methylpyridine → HCID 178515373, compound

HRID 1057692Notes

Reaction equation

HRID 1057692 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])O[C:5]2=[O:12].[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:19](=[C:16]1[CH:17]=[CH:18][NH:13][CH:14]=[CH:15]1)[C:5]2=[O:12]

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 665904-Bromophthalic anhydride

Product 1

HCID 178515373HCID 178515373, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Under N2 atmosphere, a mixture of 30 g (132 mmol) 5-bromoisobenzofuran-1,3-dione (≡4-bromophthalic acid anhydride; Apin, GB) and 12.87 ml (132 mmol) 4-picoline is heated for 15 h to 180° C. The resulting black mass is cooled to 100° C., mixed with 160 ml ethanol, boiled for 2 hours, and filtered off. The dried residue is triturated in a mortar, boiled further for 1 h in 180 ml ethanol, filtered, and washed with ethanol. The residue is dissolved at 140° C. in 90 ml DMEU, cooled, mixed with 250 ml ethyl acetate and filtered (→residue is washed out with ethyl acetate and discarded). The ethyl acetate from the filtrate is evaporated off and the residue then diluted with 260 ml acetonitrile, the title compound crystallizing out in the process: HPLC: tRet(Grad20-100)=10.4; MS (M)+=301/303.

Workup

  1. temperatureis heated for 15 h to 180° C
  2. filtrationfiltered off
  3. customThe dried residue is triturated in a mortar
  4. waitboiled further for 1 h in 180 ml ethanol
  5. filtrationfiltered
  6. washwashed with ethanol
  7. dissolutionThe residue is dissolved at 140° C. in 90 ml DMEU
  8. temperaturecooled
  9. additionmixed with 250 ml ethyl acetate
  10. filtrationfiltered (→residue
  11. washis washed out with ethyl acetate
  12. customThe ethyl acetate from the filtrate is evaporated off
  13. additionthe residue then diluted with 260 ml acetonitrile
  14. customthe title compound crystallizing out in the process

Sources & evidence

ORD record
ord-5c28248d2ed24c139857b0c06c01cf67
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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