Hydroxylamine → Ethyl 4-{4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}butanoate

HRID 219891

Reaction equation

HRID 219891 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([F:18])[CH:4]=1)#[N:2].[NH2:19][OH:20]>CCO>[NH2:2][C:1](=[N:19][OH:20])[C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([F:18])[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67529348Ethyl 4-(4-cyano-2-fluorophenoxy)butanoate

Product 1

HCID 72307473Ethyl 4-{4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}butanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(4-cyano-2-fluorophenoxy)butanoate (3.50 g; 13.93 mmol; 1 eq.) was dissolved in EtOH (70 mL). Hydroxylamine (2.05 mL; 69.65 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated under vacuum affording the title compound as a white solid. (3.82 g, 96%). 1H NMR (DMSO-d6, 300 MHz) δ 9.59 (br s, 1H), 7.49-7.43 (m, 2H), 7.18-7.12 (m, 1H), 5.80 (br s, 2H), 4.11-4.02 (m, 4H), 2.46-2.43 (m, 2H), 2.03-1.94 (quint., J=6.97 Hz, 2H), 1.20-1.15 (t, J=7.11 Hz, 3H). LC/MS (Method B): 285.1 (M+H)+. HPLC (Method A) Rt 2.67 min (Purity: 99.1%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-e1de944cb6574e5fac759cb4705b7f36
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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