Hydroxylamine → Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetate

HRID 219847Notes

Reaction equation

HRID 219847 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[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][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[C:5]([F:18])[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86645649Tert-butyl (4-cyano-2-fluorophenoxy)acetate

Product 1

HCID 72307490Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl (4-cyano-2-fluorophenoxy)acetate (3.50 g; 13.93 mmol; 1 eq.) was suspended 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 affording the title compound as a white solid (3.57 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 9.61 (br s, 1H), 7.51-7.41 (m, 2H), 7.09-7.03 (t, J=8.84 Hz 1H), 5.81 (br s, 2H), 4.78 (s, 2H), 1.42 (s, 9H). LC/MS (Method 13): 285.1 (M+H)+. HPLC (Method A) Rt 2.91 min (Purity: 94.3%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4514087895b54988b799aa5f9c2c2fd3
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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