Hydrochloric Acid → 3-[4-(2-Methyl-2-nitropropylamino)benzoyl]propionic acid

HRID 654072Notes

Reaction equation

HRID 654072 reaction equation
Cl.[NH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][CH:4]=1.[CH3:16][C:17]([N+:21]([O-:23])=[O:22])([CH3:20])[CH2:18]O.[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:16][C:17]([N+:21]([O-:23])=[O:22])([CH3:20])[CH2:18][NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64422-Methyl-2-nitro-1-propanol2×HCID 14798Sodium HydroxideHCID 678566483-(p-Aminobenzoyl)propionic acid hydrochloride

Product 1

HCID 150205023-[4-(2-Methyl-2-nitropropylamino)benzoyl]propionic acidYield 87.5%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixed solution containing 46 g of 3-(p-aminobenzoyl)propionic acid hydrochloride, 25 g of 2-methyl-2-nitro-1-propanol, 1 g of benzyl triethyl ammonium chloride, 17 g of sodium hydroxide and 40 ml of water was heated under reflux for 6 hours. Then, 12 g of 2-methyl-2-nitro-1-propanol was added, and the mixture was further heated under reflux for 18 hours. Then 20% HCl was added. The solution was acidified (pH 2). The crystals which precipitated were collected by filtration. The crystals were washed with water and recrystallized from tetrahydrofuran to give 51.6 g of 3-[4-(2-methyl-2-nitropropylamino)benzoyl]propionic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 18 hours
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration
  7. washThe crystals were washed with water
  8. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-bfad19c9884941dcaeaf79c4aaa2b7c8
Source dataset
uspto-grants-1992_07
Patent number
US05130314

Reaction notes

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