2486-69-3 → 4-Amino-3-methoxy-N-methylbenzamide

HRID 1487583Notes

Reaction equation

HRID 1487583 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)(O)[O-].[Na+].[CH3:18][N:19](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][CH3:18])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 4

HCID 2880572486-69-3HCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 204444344-Amino-3-methoxy-N-methylbenzamideYield 63%

Procedure

To a solution of 4-amino-3-methoxybenzoic acid (1 equiv) in N—N-dimethylformamide (0.6 M) was added sodium bicarbonate (9.7 equiv), HATU (2 equiv) and methyl amine hydrochloride (10 equiv). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured on water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 100-200 mesh, 0-10% MeOH in DCM as eluent) to give the title compound. (Yield: 63%). MS (ESI) m/z 181 [M+1]1.

Workup

  1. additionThe reaction mixture was poured on water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel 100-200 mesh, 0-10% MeOH in DCM as eluent)

Sources & evidence

ORD record
ord-f721ef1b44b24dee97a8104390346554
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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