Diethyl Ether → HCID 15084058, compound

HRID 1534858Notes

Reaction equation

HRID 1534858 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O-:16])(=O)[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:10].S([O-])([O-])(=O)=O.[Na+].[Na+].CCOCC.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:7][OH:16]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 24436Sodium SulfateHCID 5459842AnthranilateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15084058HCID 15084058, compoundYield 94%

Procedure

To a suspension of 0.96 g (25.3 mmol) of lithium aluminium hydride in 40 ml of dry THF was dropwise added a solution of 4.0 g (16.9 mmol) of methyl N.(3.methoxypropanoyl) anthranilate in 10 ml of dry THF under chilling with ice for a period of 15 min. The mixture was then heated under reflux for 1 hr. To the resulting mixture, a saturated aqueous sodium sulfate was added under chilling with ice to decompose the excess lithium aluminium hydride. After the addition of 40 ml of ether, insolubles were removed by sellaite filtration. The organic portion was collected and dried over anhydrous sodium sulfate, then the solvent was distilled off under reduced pressure to leave 3.1 g of the desired compound as a pale yellow oil. (Yield: 94.0 %)

Workup

  1. additionwas dropwise added a solution of 4.0 g (16.9 mmol) of methyl N.(3
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 1 hr
  4. temperatureunder chilling with ice
  5. customwere removed by sellaite filtration
  6. customThe organic portion was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f5059fa5a42f4beebc2f14b3695bf100
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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