Sodium Hydroxide → HCID 21486327, compound

HRID 1579176Notes

Reaction equation

HRID 1579176 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[OH-].[Na+].[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>C1COCC1.O>[CH:16]1([C:19]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=2)=[O:20])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 77637Cyclopropanecarbonyl chlorideHCID 2357134-Amino-2-nitrobenzoic Acid

Product 1

HCID 21486327HCID 21486327, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6 g (0.033 mol) of 4-amino-2-nitrobenzoic acid were dissolved in a mixture (100 ml) of THF and water (1:1). The solution was adjusted to pH 8.5 with 2 N NaOH and reacted at room temperature with 3.78 g (0.0363 mol) of cyclopropanecarboxylic acid chloride in 25 ml of THF. The pH value of the reaction solution was kept at 8.0 - 8.5 to the end by further addition of 2 N sodium hydroxide solution. After a reaction time of 3.5 hours, the solvent was next distilled off. The residue was diluted with water and the aqueous solution was extracted by shaking once with ethyl acetate and was finally acidified with 2 N HCl to pH 2.0. The oil which precipitated was isolated by extraction with ethyl acetate. After washing and drying the ethyl acetate phase, the solution was concentrated to dryness. The product was crystallized from ethyl acetate/petroleum ether.

Workup

  1. distillationAfter a reaction time of 3.5 hours, the solvent was next distilled off
  2. additionThe residue was diluted with water
  3. extractionthe aqueous solution was extracted
  4. customThe oil which precipitated
  5. customwas isolated by extraction with ethyl acetate
  6. washAfter washing
  7. dry with materialdrying the ethyl acetate phase
  8. concentrationthe solution was concentrated to dryness
  9. customThe product was crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-531a20de59cd4a92837c87f3889bb9b1
Source dataset
uspto-grants-1976_01
Patent number
US03931153

Reaction notes

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