1,2-Dichloroethane → HCID 21405271, compound

HRID 1887700Notes

Reaction equation

HRID 1887700 reaction equation
[N+:1]([C:4]1[CH:12]=[N:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:26][C:24]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:24][NH:26][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][N:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27629243-nitroisonicotinic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 21405271HCID 21405271, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 3-nitroisonicotinic acid (4.78 g, 28.4 mmol), methylamine hydrogen chloride (2.88 g, 1.5 eq), EDC (6.53 g, 1.2 eq), HOBt (4.59 g, 1.2 eq) in DMF (50 mL) was added DIEA (25 mL, 5.0 eq). The mixture was stirred at room temperature overnight. It was concentrated and the crude was dissolved in EtOAc. It was washed with saturated NaHCO3 solution. The solvent was removed and the crude was purified by silica gel chromatography (0%˜20% MeOH/DCM) to obtain the desired product N-methyl-3-nitroisonicotinamide (878 mg, isolated yield 17%).

Workup

  1. concentrationIt was concentrated
  2. dissolutionthe crude was dissolved in EtOAc
  3. washIt was washed with saturated NaHCO3 solution
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (0%˜20% MeOH/DCM)

Sources & evidence

ORD record
ord-7c70c95b5f884caa9f880d7577dfbc95
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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