Triethylamine → HCID 178490401, compound

HRID 585091Notes

Reaction equation

HRID 585091 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.Cl.[NH2:13][OH:14].C(N(CC)CC)C>C(O)C>[OH:14][NH:13][C:10](=[NH:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178490401HCID 178490401, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4-methoxyphenyl)acetonitrile (2.00 g, 14 mmol) and hydroxylamine hydrochloride (1.94 g, 28 mmol) in ethanol (25 mL) was treated with triethylamine (4.4 mL) and heated at reflux for 16 hours after which the solvent was evaporated under reduced pressure. Sodium carbonate solution (10%, 100 mL) was added and the solution extracted with ethyl acetate (150 mL). The organic extract was dried, filtered and evaporated under reduced pressure to give a green solid which was purified by recrystallization from ethyl acetate/hexane to give 1.43 g (57%) of (Via) as pale green prisms. mp 163-170° C. (lit.14 108-109°). MS m/z 181 (M+1)+

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours after which the solvent
  3. customwas evaporated under reduced pressure
  4. additionSodium carbonate solution (10%, 100 mL) was added
  5. extractionthe solution extracted with ethyl acetate (150 mL)
  6. extractionThe organic extract
  7. customwas dried
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a green solid which
  11. customwas purified by recrystallization from ethyl acetate/hexane
  12. customto give 1.43 g (57%) of (Via) as pale green prisms
  13. custommp 163-170° C. (lit.14 108-109°)

Sources & evidence

ORD record
ord-75460f0fbd74488fb385d6217c1806e5
Source dataset
uspto-grants-2005_08
Patent number
US06930118B2

Reaction notes

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