Ethanolamine → HCID 12906351, compound

HRID 1390674Notes

Reaction equation

HRID 1390674 reaction equation
[C:1]([CH:3]1[CH:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:5]([C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4]1)#[N:2].[CH2:19]([CH2:21]N)[OH:20]>C1C=CC=CC=1.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[O:20]1[CH2:19][CH2:21][N:2]=[C:1]1[CH:3]1[CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]([C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:4]1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 2403063008-09-1

Product 1

HCID 12906351HCID 12906351, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 241BenzeneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 11-cyano-9,10-dihydro-9,10-ethanoanthracene (4.6 g), ethanolamine (1.8 g) and zinc acetate (250 mg) is stirred at 130° C. for 5 hours. The reaction mixture is dissolved in benzene and passed through a column of 10% hydrated alumina. The eluate is evaporated to remove the solvent, and the residue is recrystallized from ether to give 11-(2-oxazolin-2-yl)-9,10-dihydro-9,10-ethanoanthracene (3.3 g) as crystals melting at 155 to 156° C. IR (KBr), 1655 cm-1 (O--C=N).

Workup

  1. customThe eluate is evaporated
  2. customto remove the solvent
  3. customthe residue is recrystallized from ether

Sources & evidence

ORD record
ord-eb8b60e2ca8b472683fd3998f6cda1ed
Source dataset
uspto-grants-1979_02
Patent number
US04139711

Reaction notes

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