Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67249010, compound

HRID 335782Notes

Reaction equation

HRID 335782 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:20]=[CH:19][C:18]3[O:17][C:16]4[CH:15]=[CH:14][NH:13][C:12](=[O:21])[C:11]=4[C:10](=O)[C:9]=3[CH:8]=2)[CH:2]=1.[CH3:23][Mg]Br.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.ClCCCl>[CH2:23]=[C:10]1[C:11]2[C:12](=[O:21])[NH:13][CH:14]=[CH:15][C:16]=2[O:17][C:18]2[CH:19]=[CH:20][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:8][C:9]1=2

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67248230HCID 67248230, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67249010HCID 67249010, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8-(pyridin-3-yl)-1H-chromeno[3,2-c]pyridine-1,10(2H)-dione (0.100 g, 0.345 mmol) in THF (3.00 mL) was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether) (0.345 mL, 1.034 mmol) was added dropwise. The mixture stirred at 0° C. for 1 h. The mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution and diluted with ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a tan solid. The material was dissolved in 1,2-dichloroethane (3.00 mL), pyridinium p-toluenesulfonate (8.66 mg, 0.034 mmol) was added, and the mixture was heated at reflux for 2 h to afford a tan suspension. This mixture was filtered, and the solids were washed with 1,2 dichloroethane and dried to afford 10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one as a tan solid. MS m/z=289.0 [M+H]+. Calcd for C18H12N2O2: 288.1.

Workup

  1. customThe mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution
  2. additiondiluted with ethyl acetate
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a tan solid
  10. temperaturethe mixture was heated
  11. temperatureat reflux for 2 h
  12. customto afford a tan suspension
  13. filtrationThis mixture was filtered
  14. washthe solids were washed with 1,2 dichloroethane
  15. customdried

Sources & evidence

ORD record
ord-0639de113e7c49e884c7a61e4c4097fe
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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