4-Methylmorpholine → 2-Methoxy-N-(6-methylpyridin-3-yl)methyl-4-nitrobenzamide

HRID 1924960Notes

Reaction equation

HRID 1924960 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:44][C:45]1[N:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=1>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([NH:52][CH2:51][C:48]1[CH:49]=[N:50][C:45]([CH3:44])=[CH:46][CH:47]=1)=[O:7]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757764-Nitro-o-anisic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12214337(6-Methylpyridin-3-yl)methanamine

Product 1

HCID 575899912-Methoxy-N-(6-methylpyridin-3-yl)methyl-4-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-4-nitrobenzoic acid (293 mg, 1.49 mmol) is dissolved in DMF (2 mL) and 4-methylmorpholine (220 μL, 3.0 mmol) and TBTU (1.79 g, 1.7 mmol) are added. The mixture is stirred at rt for 30 min and C-(6-methylpyridin-3-yl)methylamine (400 mg, 3.27 mmol) is added. Stirring is continued at rt for 12 h. DCM (10 mL) is added and the organic phase is washed with Na2CO3 (5% aq.), HCl (3% aq.) and water, and then dried over Na2SO4. After evaporation of the solvents, the residue is triturated with ether-hexane to afford the title compound as a white solid.

Workup

  1. stirringStirring
  2. waitis continued at rt for 12 h
  3. washthe organic phase is washed with Na2CO3 (5% aq.), HCl (3% aq.) and water
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation of the solvents
  6. customthe residue is triturated with ether-hexane

Sources & evidence

ORD record
ord-36f7f9ce126c42fe869cb8b7706051c7
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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