O-(2,4-dinitrophenyl)hydroxylamine → HCID 86671435, compound

HRID 876813Notes

Reaction equation

HRID 876813 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[O:28]N)([O-:18])=[O:17]>CC#N>[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[O-:28])([O-:18])=[O:17].[NH2:16][N+:13]1[CH:12]=[CH:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridine

Product 1

HCID 86671435HCID 86671435, compoundYield 203.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-((tert-butyldimethylsilyloxy)methyl)pyridine (8.9 g, 39.7 mmol) and O-(2,4-dinitrophenyl)hydroxylamine Y-3 (7.9 g, 39.7 mmol) in MeCN (27 ml) was stirred at 40° C. for 24 h, then concentrated to afford the title compound (17.1 g), used in next step without further purification. MS (m/z): 239(M−183)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0508233c344e463d83bd9bec355dd36c
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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