Ethanolamine → HCID 70573308, compound

HRID 262447Notes

Reaction equation

HRID 262447 reaction equation
[I-].C[N+:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:5]=2[CH:4]=1.C(CN)O>O>[CH:4]1[C:5]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[C:6]=2[CH:7]=[CH:8][N:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 70572305HCID 70572305, compound2×

Product 1

HCID 70573308HCID 70573308, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 19.9 g 2-methyl-9H-dibenzo[1,2;5,6]cyclohepta[3,4-c]pyridinium iodide (formula IV) and 100 ml ethanolamine is heated with stirring in an oil bath at 160° C. for 2 hours. The reaction mixture is then poured out into H2O and extracted with ether. The organic phase is extracted with dilute HCl, after which the acid aqueous layer is made alkaline and extracted with ether. The ether layer is washed with H2O until neutral, dried over Na2SO4 and evaporated to dryness. Yield: 7.74 g. 9H-dibenzo[1,2;5,6]cyclopenta[3,4-c]pyridine (formula IVA). The residue is crystallized from ethyl acetate/petroleum ether (1:2).

Workup

  1. temperatureis heated
  2. extractionextracted with ether
  3. extractionThe organic phase is extracted with dilute HCl
  4. extractionextracted with ether
  5. washThe ether layer is washed with H2O until neutral,
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue is crystallized from ethyl acetate/petroleum ether (1:2)

Sources & evidence

ORD record
ord-b0fe02504d044c84a1211fcd7521b61f
Source dataset
uspto-grants-1979_05
Patent number
US04154836

Reaction notes

Loading…