2-Methylbenzoic acid → N-methoxy-N,2-dimethylbenzamide

HRID 1795108Notes

Reaction equation

HRID 1795108 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:11]CN=C=NCCCN(C)C.Cl.Cl.[CH3:24][N:25](C)[OH:26]>CN(C1C=CN=CC=1)C.CC(N(C)C)=O.C(Cl)Cl>[CH3:11][O:26][N:25]([CH3:24])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

7

Reactant 3

HCID 83732-Methylbenzoic acidHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11344340N-methoxy-N,2-dimethylbenzamideYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

To a premixed solution of 2-methylbenzoic acid (7.5 mmol), EDCl (1.5 mmol) and DMAP (3.0 mmol) in DMA 40 mL and DCM 13 mL is added dimethylhydroxylamine hydrochloride (1.5 mmol). The reaction is stirred at room temperate over night. The reaction mixture is then filtered. The filtrate is diluted with EtOAc and washed with water, 10% NaHSO4 and brine. The solution is dried over Na2SO4 and the solvent is evaporated. A light yellow oil N-methoxy-N,2-dimethylbenzamide is obtained in 80% yield.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. additionThe filtrate is diluted with EtOAc
  3. washwashed with water, 10% NaHSO4 and brine
  4. dry with materialThe solution is dried over Na2SO4
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-548fb378cca44d19b7489825178c8f1d
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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