Hydroxylamine → Ethyl 4-{3-[amino(hydroxyimino)methyl]phenoxy}butanoate

HRID 219893Notes

Reaction equation

HRID 219893 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:2].[NH2:18][OH:19]>CCO>[NH2:2][C:1](=[N:18][OH:19])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 57708764HCID 57708764, compound

Product 1

HCID 72307492Ethyl 4-{3-[amino(hydroxyimino)methyl]phenoxy}butanoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(3-cyanophenoxy)butanoate (3.79 g; 16.25 mmol; 1 eq.) was suspended in EtOH (75.80 mL). Hydroxylamine (2.40 mL; 81.24 mmol; 5 eq.) was added in one portion and the reaction mixture was stirred at RT for 24 hours. The reaction mixture was concentrated affording the title compound as a white solid (4.29 g, 99%). 1H NMR (DMSO-d6, 300 MHz) δ 9.61 (br s, 1H), 7.27-7.20 (m, 3H), 6.94-6.90 (m, 1H), 5.79 (br s, 2H), 4.11-3.98 (m, 4H), 2.48-2.44 (t, J=7.15 Hz, 2H), 2.01-1.93 (m, 2H), 1.20-1.15 (t, J=7.03 Hz, 3H). LC/MS (Method A): 266.8 (M+H)+. HPLC (Method A) Rt 2.62 min (Purity: 98.8%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-8ef754dedd5b4ac689dfcbe29c9b44ac
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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