Hydrochloric Acid → gamma-[4-(2-Methyl-2-nitropropylamino)benzoyl]butyric acid

HRID 1905419Notes

Reaction equation

HRID 1905419 reaction equation
Cl.[NH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=1.[CH3:17][C:18]([N+:22]([O-:24])=[O:23])([CH3:21])[CH2:19]O.[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:17][C:18]([N+:22]([O-:24])=[O:23])([CH3:21])[CH2:19][NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64422-Methyl-2-nitro-1-propanolHCID 14798Sodium HydroxideHCID 67899846gamma-(p-Aminobenzoyl)butyric acid hydrochloride

Product 1

HCID 14578679gamma-[4-(2-Methyl-2-nitropropylamino)benzoyl]butyric acidYield 82.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of γ-(p-aminobenzoyl)butyric acid hydrochloride (349.5 g), 2-methyl-2-nitro-1-propanol (222 g), sodium hydroxide (114.8 g), benzyltriethyl ammonium chloride (6.35 g) and water (1.5 liters) was refluxed for 40 hours. Concentrated hydrochloric acid (170 ml) was added to the reaction mixture to acidify it. The precipitated crystals were collected by filtration to give γ-[4-(2-methyl-2-nitropropylamino)benzoyl]butyric acid (364.46 g).

Workup

  1. temperaturewas refluxed for 40 hours
  2. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-bca71cbd5a38482dac3260419ad484bd
Source dataset
uspto-grants-1989_06
Patent number
US04843072

Reaction notes

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