Hydrochloric Acid → Ethyl α-(hydroxyimino)-2-nitrobenzeneacetate

HRID 1721812Notes

Reaction equation

HRID 1721812 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([O-:3])=[O:2].[N:16](OCCC(C)C)=[O:17].[O-]CC.[Na+].[Na].Cl>C(O)C.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[N:16][OH:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 595882Ethyl 2-nitrophenylacetateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 53403224Ethyl α-(hydroxyimino)-2-nitrobenzeneacetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

A mixture of 50 g of ethyl (2-nitrophenyl)acetate, 30 g of isoamyl nitrite and 400 ml of ethanol was added to sodium ethoxide prepared by treating 5.1 g of sodium with 100 ml of ethanol and diluting with ethanol to 100 ml. The mixture was heated at 50°-60° C. for 4 hours, cooled, 400 ml of water was added, the mixture was acidified with 6N hydrochloric acid and extracted with ether. The extract was stripped of solvent, and the residue was recrystallized from benzene to give ethyl (2-nitrophenyl)glyoxylate oxime (3A), as a white solid, m.p.: 167°-168° C.

Workup

  1. customprepared
  2. temperatureThe mixture was heated at 50°-60° C. for 4 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-ee7926cc2ef44d1288995b7421883d16
Source dataset
uspto-grants-1989_08
Patent number
US04853027

Reaction notes

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