Hydroxylamine → N-Hydroxy-2-[1-(3-methyl-butyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetamide

HRID 2105546Notes

Reaction equation

HRID 2105546 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]1=[O:20].[NH2:22][OH:23].[OH-].[Na+]>C1COCC1>[OH:23][NH:22][C:3](=[O:2])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]1=[O:20]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 69003096[1-(3-Methyl-butyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester

Product 1

HCID 11312326N-Hydroxy-2-[1-(3-methyl-butyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude [1-(3-methyl-butyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester obtained in the previous step is dissolved in 0.5 mL of anhydrous THF. Freshly prepared NH2OH (0.77 M in MeOH) (0.44 mL) (also containing 0.77M NaOH) is then added and the mixture is stirred at room temperature for 12 hours. The final product N-hydroxy-2-[1-(3-methyl-butyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetamide is obtained by preparative LC/MS using 1 to 99% ACN as gradient. 1H NMR (400 MHz, MeOD): δ 7.29 (t, 1H), 7.20 (d, 1H), 7.11 (d, 1H), 7.04 (t, 1H), 3.97 (m, 2H), 3.02-2.89 (m, 2H), 2.77-2.65 (m, 2H), 2.17 (dd, 1H), 1.65 (m, 1H), 1.50 (m, 2H), 0.97 (2d, 6H). MS: (ES+): 291.3 [M+1].

Workup

  1. additionis then added

Sources & evidence

ORD record
ord-2bb8399d0a834a079920a29ff391f469
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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