O-ethylhydroxylamine hydrochloride → 3-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamide

HRID 39502Notes

Reaction equation

HRID 39502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[N:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[C:4]([CH3:18])[CH:3]=1.CCN(C(C)C)C(C)C.Cl.[CH2:29]([O:31][NH2:32])[CH3:30]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[N:16][CH:15]=[CH:14][C:10]=2[C:11]([NH:32][O:31][CH2:29][CH3:30])=[O:13])=[C:4]([CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 576496333-[(4-Bromo-2-methylphenyl)amino]isonicotinic acid

Product 1

HCID 576496563-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamideYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(4-Bromo-2-methylphenyl)amino]isonicotinic acid 2b (320 mg, 1.04 mmol) was dissolved in 15 ml dry DMF followed by the addition of DIPEA (2.08 mmol, 373 μl), ByBOP (1.25 mmol, 651 mg) and O-ethylhydroxylamine hydrochloride (2.08 mmol, 203 mg). The mixture was stirred for 2 h and the volatiles were removed in vacuo. The crude material was purified by flash chromatography using silica gel and a gradient of 0-5% methanol in DCM as eluent to give 280 mg (800 μmol; 77% yield) of pure desired product.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-a378343087dd4af4ba59321716dc3025
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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