Hydrochloric Acid → 4-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochloride

HRID 1410041Notes

Reaction equation

HRID 1410041 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:4][C:3]1=[O:21].O.[ClH:23]>>[ClH:23].[NH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:21])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 683791842-(2-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 683792224-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochlorideYield 85%

Procedure

2-(2-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)isoindoline-1,3-dione (230 mg, 0.8 mmol) in conc. HCl (25 mL) was stirred at 95° C. for 18 hours. H2O (20 mL) was added and then extracted with ethyl acetate (3×30 mL). The aqueous was concentrated under reduce pressure to give 4-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochloride (130 mg, 85%). LC-MS: 153 [M+H]+, tR=0.42 min.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. concentrationThe aqueous was concentrated

Sources & evidence

ORD record
ord-53c44d91470f448c90cc7a8dba90a2f4
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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