Benzene → HCID 21493497, compound

HRID 1973243Notes

Reaction equation

HRID 1973243 reaction equation
C(O[CH:5]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)(=O)C.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C1C=CC=CC=1>CCOCC>[N:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][CH:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[O:12][C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 773174-PyridinemethanamineHCID 125434549-Acetoxyxanthene

Product 1

HCID 21493497HCID 21493497, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.0 g. of 9-acetoxyxanthene and 2.0 g. of 4-aminomethylpyridine in 100 ml. of benzene is refluxed for 24 hours. The reaction mixture is stripped of solvent and the residue dissolved in ether. The ether solution is washed with cold 5% sodium carbonate and water and dried over potassium carbonate and chromatographed with alumina and eluting with ether/hexane. The eluate is extracted with ether/acetone and concentrated in vacuo to give 4-pyridylmethyl-9-xanthylamine having a m.p. of 83°-85° C.

Workup

  1. washThe ether solution is washed with cold 5% sodium carbonate and water
  2. dry with materialdried over potassium carbonate
  3. customchromatographed with alumina
  4. washeluting with ether/hexane
  5. extractionThe eluate is extracted with ether/acetone
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df8b736bc1d94768b8572548e97d17a2
Source dataset
uspto-grants-1976_12
Patent number
US03996364

Reaction notes

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