Methylamine → 3-Methoxy-N-methyl-4-nitrobenzamide

HRID 1480868Notes

Reaction equation

HRID 1480868 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:30](O)=[O:31].CCN(C(C)C)C(C)C.CN>C1COCC1>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:30]([NH:2][CH3:1])=[O:31]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 787643-Methoxy-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 568324173-Methoxy-N-methyl-4-nitrobenzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

HATU (0.501 g, 1.319 mmol) was added to a solution of 3-methoxy-4-nitrobenzoic acid (0.2 g, 1.014 mmol), DIPEA (0.265 mL, 1.522 mmol) and 2M methylamine solution in THF (1.0 mL, 2.029 mmol) in THF (2.7 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and purified by Biotage silica gel column chromatography eluting with DCM/EtOAc 80/20 to 60/40 followed by a second chromatography eluting with cyclohexane/EtOAc 50/50 to 40/60 to afford the title compound as a white solid (166 mg, 78%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by Biotage silica gel column chromatography
  3. washeluting with DCM/EtOAc 80/20 to 60/40
  4. washeluting with cyclohexane/EtOAc 50/50 to 40/60

Sources & evidence

ORD record
ord-f4fca66906d74b8dbbbb09870a4d3151
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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