Hydrochloric Acid → HCID 19704898, compound

HRID 2255916Notes

Reaction equation

HRID 2255916 reaction equation
[CH3:1][O:2][C:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5](=[O:15])[CH:4]=1.[Cl-].[Li+].[CH:18](NC(C)C)(C)C.C([Li])CCC.CI.Cl>O.O1CCCC1>[CH3:1][O:2][C:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5](=[O:15])[C:4]=1[CH3:18]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 433294Lithium ChlorideHCID 107506631H-1-Benzazepine-2,5-dione, 3-methoxy-HCID 178418339Butyllithium

Product 1

HCID 19704898HCID 19704898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

3-Methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.5 g) and anhydrous lithium chloride (0.63 g) were added to dry tetrahydrofuran (10 mL), and the mixture was cooled to -70° C. To this was added diisopropylamine (380 mL), followed by butyllithium (2.2 mL, 2.5M in hexanes); and the mixture was warmed to -20° C. After 30 minutes, methyl iodide (307 mL) was added and the mixture cooled to -10° C. for 10 minutes. The mixture was diluted with water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The solid was purified by chromatography, with ethyl acetate:toluene (1:1) as the eluent, and recrystallized from hot toluene to give the methylated product as a white solid (0.367 g); NMR: 2.03 (s,3); MS(EI): m/z=217(M).

Workup

  1. temperatureand the mixture was warmed to -20° C
  2. temperaturethe mixture cooled to -10° C. for 10 minutes
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. customevaporated
  7. customThe solid was purified by chromatography, with ethyl acetate:toluene (1:1) as the eluent
  8. customrecrystallized from hot toluene

Sources & evidence

ORD record
ord-773abca81d7e4ded838d3e979a412612
Source dataset
uspto-grants-1997_08
Patent number
US05654295

Reaction notes

Loading…