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

HRID 219850Notes

Reaction equation

HRID 219850 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8])#[N:2].[NH2:20][OH:21]>C(O)C>[NH2:2][C:1](=[N:20][OH:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:7]([CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 77231477Tert-butyl [(3-cyanobenzyl)(methyl)amino]acetate

Product 1

HCID 72307500Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl [(3-cyanobenzyl)(methyl)amino]acetate (9 g, 34.6 mmol) in ethanol (60 mL) under N2, was added hydroxylamine (6 g, 178.8 mmol) in one portion. After being stirred at RT for 12 h, the reaction mixture was concentrated under reduced pressure to afford a colorless oil. It was triturated in diisopropyl ether, affording the title product as a white solid that was filtrated and dried under vacuo (8.5 g, 84%). 1H NMR (DMSO-d6, 300 MHz) δ 9.57 (1H, s), 7.59 (1H, s), 7.52-7.53 (1H, m), 7.29-7.31 (2H, m), 5.75 (2H, s), 3.61 (2H, s), 3.15 (2H, s), 2.23 (3H, s), 1.41 (9H, s). LC/MS (Method A): 294.0 (M+H)+. HPLC (Method B) Rt 3.31 min (Purity: 97.5%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto afford a colorless oil
  3. customIt was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-892d1af922304039a7b8069bb18ccdcd
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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