Ethanol → HCID 12919745, compound

HRID 848215Notes

Reaction equation

HRID 848215 reaction equation
[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH:13](Br)Br)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].CC[OH:18]>[N+]([O-])([O-])=O.[Ag+].O>[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH:13]=[O:18])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 702EthanolHCID 12919743HCID 12919743, compound

Product 1

HCID 12919745HCID 12919745, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A mixture of 6 (9.8 g, 0.024 mol), AgNO3 (8.8 g, 0.052 mol), EtOH (100 ml) and H2O (25 mL) was heated on a steam bath for 1 hour. The yellow solid was filtered and the solution concentrated to dryness. The residue was treated with H2O and extracted with CHCl3 (3X). The organic layer was dried, filtered and concentrated to dryness. Distillation of the resulting oil at 105°-135° C. at 0.5 mm gave 3.0 g (48%) of 3; 1H NMR (CDCl3) 1.45δ(3H, t, J=7), 4.4 (2H, q, J=7, 8.6 (1H, d, J=2),/8.9 (1H, d, J =2) and 10.1 (1H, s).

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. filtrationThe yellow solid was filtered
  3. concentrationthe solution concentrated to dryness
  4. additionThe residue was treated with H2O
  5. extractionextracted with CHCl3 (3X)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. distillationDistillation of the resulting oil at 105°-135° C. at 0.5 mm

Sources & evidence

ORD record
ord-05d381b2dcbd419bb2f97774b142a164
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

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