Water → 9-Methylaminoxanthen

HRID 1284292Notes

Reaction equation

HRID 1284292 reaction equation
[CH:1]([NH:3][CH:4]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][NH:3][CH:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:11][C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 602540N-9H-Xanthen-9-ylformamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 202040099-Methylaminoxanthen

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9-formamidoxanthen (30.5 g.) in tetrahydrofuran (400 ml.) was added to a suspension of lithium aluminium hydride (5.2 g.) in tetrahydrofuran (100 ml.) at room temperature. The mixture was stirred and refluxed for 5 hours, left to stand at room temperature overnight and then decomposed by the addition of water (5.2 ml.), 5N sodium hydroxide solution (4 ml.) and water (16.8 ml.). The suspension was filtered, the solid was washed with ether, and the combined filtrate and washings were evaporated. The residual syrup was dissolved in ether and extracted into 3N acetic acid solution (500 ml.) at 5° - 10°C. The aqueous extract was basified, the oil which separated was collected in ether and the dried, ethereal extract was evaporated. The residue was distilled to give 9-methylaminoxanthen, b.p. (bath) 110°C./0.1 mm.

Workup

  1. temperaturerefluxed for 5 hours
  2. waitleft
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with ether
  5. customthe combined filtrate and washings were evaporated
  6. dissolutionThe residual syrup was dissolved in ether
  7. extractionextracted into 3N acetic acid solution (500 ml.) at 5° - 10°C
  8. extractionThe aqueous extract
  9. customthe oil which separated
  10. customwas collected in ether
  11. extractionthe dried, ethereal extract
  12. customwas evaporated
  13. distillationThe residue was distilled

Sources & evidence

ORD record
ord-09ec6b888e1b4f63a4badb873926d686
Source dataset
uspto-grants-1976_08
Patent number
US03978226

Reaction notes

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