HCID 13827107, compound → HCID 13827108, compound

HRID 2351283Notes

Reaction equation

HRID 2351283 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([CH2:21][CH3:22])[C:8]=1[C:9]([O:11]CC)=[O:10])=[O:5])[CH3:2]>O1CCCC1.[OH-].[Na+]>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([CH2:21][CH3:22])[C:8]=1[C:9]([OH:11])=[O:10])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13827107HCID 13827107, compound

Product 1

HCID 13827108HCID 13827108, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 2-ethoxycarbonylamino-4-nitro-6-ethyl-benzoate in tetrahydrofuran (10 ml) and sodium hydroxide (20 ml, 10%) was stirred at room temperature for 20 hours. The solution was extracted with ethyl acetate. The aqueous layer was acidified to pH=1 with 6M HCl, and then immediately extracted with ethylacetate. The ethyl acetate extract was washed with water and dried over magnesium sulphate. Solvent evaporation gave a solid which was further recrystallized from methylene chloride: petroleum ether to yield 2-ethoxycarbonylamino-4-nitro-6-ethyl benzoic acid, m.p. 121°-123° C. as orange crystals. IR νmax : 1665, 1720, 1620, 1510, 2500-3200(br), 3500cm.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. extractionimmediately extracted with ethylacetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulphate
  6. customSolvent evaporation
  7. customgave a solid which
  8. customwas further recrystallized from methylene chloride

Sources & evidence

ORD record
ord-7662243cd25740088149a205f21452f2
Source dataset
uspto-grants-1989_10
Patent number
US04873232

Reaction notes

Loading…