4-Methylpyridine → HCID 178515373, compound

HRID 1384117Notes

Reaction equation

HRID 1384117 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>>[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

3

Reactant 2

HCID 79634-MethylpyridineHCID 665904-Bromophthalic anhydride

Product 1

HCID 178515373HCID 178515373, compound

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. filtrationfiltered
  5. washwashed with ethanol
  6. dissolutionThe residue is dissolved at 140° C. in 90 ml DMEU
  7. temperaturecooled
  8. additionmixed with 250 ml ethyl acetate
  9. filtrationfiltered (→residue
  10. washis washed out with ethyl acetate
  11. customThe ethyl acetate from the filtrate is evaporated off
  12. additionthe residue then diluted with 260 ml acetonitrile
  13. customthe title compound crystallizing out in the process

Sources & evidence

ORD record
ord-c4a605b676494c55957085cb36cec92f
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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