Methyl Methacrylate → HCID 21252827, compound

HRID 1530989Notes

Reaction equation

HRID 1530989 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[C:17](OC)(=[O:21])[C:18]([CH3:20])=[CH2:19]>O1CCCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:21])[C:18]([CH3:20])=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3

Participants

4

Reactant 2

HCID 6658Methyl MethacrylateHCID 21252868HCID 21252868, compound

Product 1

HCID 21252827HCID 21252827, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-bromo-6-methoxycarbazole (4 g) produced in Example 101, step 4 was dissolved in anhydrous tetrahydrofuran (32 ml), and to the solution were added methyl methacrylate (12.4 ml) and then Triton B (1.12 ml). The mixture was heated under reflux in an argon atmosphere for 1 hour, and the solvent was evaporated under reduced pressure. The resulting residue was suspended in methanol (40 ml), and sodium hydroxide (1 g) dissolved in water (13 ml) was added dropwise to the solution at room temperature, and the mixture was heated under reflux for 4 hours. The solvent was evaporated under reduced pressure, and water and ether were added for phase separation. The aqueous layer was rendered acidic by addition of 1N hydrochloric acid, and ethyl acetate was added for extraction. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane and recovered by filtration to obtain the title compound (4.0 g, 95%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 1 hour
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionsodium hydroxide (1 g) dissolved in water (13 ml)
  5. additionwas added dropwise to the solution at room temperature
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 4 hours
  8. customThe solvent was evaporated under reduced pressure, and water and ether
  9. additionwere added for phase separation
  10. additionThe aqueous layer was rendered acidic by addition of 1N hydrochloric acid, and ethyl acetate
  11. additionwas added for extraction
  12. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  13. dry with materialdried over anhydrous sodium sulfate
  14. customthe solvent was evaporated under reduced pressure
  15. washThe residue was washed with hexane
  16. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-4af213236d814694ab51714a0e27137b
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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