Hydroxylamine → Tert-butyl (2-{3-[amino(hydroxyimino)methyl]phenyl}ethoxy)acetate

HRID 219889Notes

Reaction equation

HRID 219889 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:20][OH:21]>CCO>[NH2:2][C:1](=[N:20][OH:21])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86645650Tert-butyl [2-(3-cyanophenyl)ethoxy]acetate

Product 1

HCID 72307498Tert-butyl (2-{3-[amino(hydroxyimino)methyl]phenyl}ethoxy)acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-butyl [2-(3-cyanophenyl)ethoxy]acetate obtained in step 1 (1.42 g; 5.43 mmol) was dissolved in EtOH (28.40 mL) to which was added hydroxylamine (401.26 μL; 50%, 27.17 mmol). Reaction mixture was stirred at RT for 18 h after which solvents were removed under vacuum, solubilized in a water/ACN mixture (1:1) and lyophilized to give the desired compound as a sticky colorless oil (1.32 g; 82%). 1H NMR (DMSO-d6, 300 MHz) δ 9.56 (bs, 1H), 7.53-7.48 (m, 2H), 7.27-7.25 (m, 2H), 5.76 (bs, 2H), 3.96 (s, 2H), 3.67 (t, J=6.9 Hz, 2H), 2.83 (t, J=6.5 Hz, 2H). LC/MS (Method B): 295.2 (M+H)+.

Workup

  1. customReaction mixture
  2. customwere removed under vacuum

Sources & evidence

ORD record
ord-9a45e10e21ad4e709d27c1d155c5a384
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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