4-Methoxy-2-nitroaniline → [(4-Methoxy-2-nitrophenyl)imino]ethyl acetate

HRID 1847078Notes

Reaction equation

HRID 1847078 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[C:13]([O:17][CH2:18][CH:19]=[N:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])(=[O:16])[CH3:14]

Participants

4

Reactant 2

HCID 667934-Methoxy-2-nitroanilineHCID 86599969Ethyl glyoxylate toluene

Product 1

HCID 86725002[(4-Methoxy-2-nitrophenyl)imino]ethyl acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxy-2-nitroaniline (1.68 g, 10.0 mmol), ethyl glyoxylate/toluene solution (50 wt %, 1.98 ml, 10.0 mmol) and toluene (20 ml) was heated under reflux under a nitrogen gas atmosphere for 17 hours while removing water using a Dean-Stark apparatus. The solvent was removed under reduced pressure to yield [(4-methoxy-2-nitrophenyl)imino]ethyl acetate crude product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under a nitrogen gas atmosphere for 17 hours
  3. customwhile removing water using a Dean-Stark apparatus
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cffe90dd2da54221bfbcd4ac685f7f72
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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