Ethanol → HCID 13827104, compound

HRID 978351Notes

Reaction equation

HRID 978351 reaction equation
[CH2:1]([C:3]1[C:4]2[C:8]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)=[N:7][O:6][CH:5]=2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:5](=[O:6])[C:4]1[C:3]([CH2:1][CH3:2])=[CH:11][C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:8]=1[NH2:7])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 13827101HCID 13827101, compound

Product 1

HCID 13827104HCID 13827104, compound

Procedure

4-ethyl-6-nitro anthranil (2 g) was refluxed for three hours in ethanol with potassium carbonate. The reaction mixture was cooled, filtered and evaporated to a dark oily solid which was dissolved in ethyl acetate and dried. The residue was re-dissolved in methylene chloride and columned on silica gel using 15% ethyl acetate-petroleum ether. The residue from the filtrate was recrystallized from methylene chloride-petroleum ether to give 1.9 g ethyl-2-amino-6-ethyl-4-nitrobenzoate, m.p. 68°-70° C., IR: 3490 cm, 3380 cm, 3080 cm, 2980 cm, 1690 cm, 1620 cm, 1515 cm, 1350 cm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customevaporated to a dark oily solid which
  4. dissolutionwas dissolved in ethyl acetate
  5. customdried
  6. dissolutionThe residue was re-dissolved in methylene chloride
  7. customThe residue from the filtrate was recrystallized from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-534a63e4f19e4e4b84932b2af78e840b
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

Loading…