5-Nitrosalicylic acid → HCID 12512105, compound

HRID 1458207Notes

Reaction equation

HRID 1458207 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OCC)(OCC)O[CH2:16][CH3:17]>>[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([O:11][CH2:16][CH3:17])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 73185-Nitrosalicylic acidHCID 31214Ethyl orthoformate

Product 1

HCID 12512105HCID 12512105, compound

Procedure

1.5 kg (8.2 mol) of 5-nitrosalicylic acid was dissolved in 2000 ml of triethyl orthoformate. The obtained solution was refluxed under heating for 3 hours to remove formed ethanol by distillation. The reaction mixture was cooled and then concentrated under reduced pressure. The obtained residue was crystallized from isopropyl ether to give 1.74 kg of the title compound as a colorless crystal.

Workup

  1. temperatureThe obtained solution was refluxed
  2. temperatureunder heating for 3 hours
  3. customto remove
  4. customformed ethanol
  5. distillationby distillation
  6. temperatureThe reaction mixture was cooled
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-1907dfa786f641a0b32548e999482cb1
Source dataset
uspto-grants-1998_12
Patent number
US05849912

Reaction notes

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