(3,4-Dimethoxyphenyl)acetic acid → 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide

HRID 2178027Notes

Reaction equation

HRID 2178027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[CH3:16][NH:17][O:18][CH3:19].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([N:17]([O:18][CH3:19])[CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 112186512-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamideYield 30.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3,4-dimethoxyphenyl)acetic acid (1 g, 5.1 mmol), N,O-dimethylhydroxylamine hydrochloride (480 mg, 5.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (978 mg, 5.1 mmol), hydroxybenzotriazole (690 mg, 5.1 mmol) and triethylamine (2.57 g, 25.5 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=8:1) to afford 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide (370 mg, yield 30.3%).

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (PE:EtOAc=8:1)

Sources & evidence

ORD record
ord-bf600264678e44789516a0fb1cfe06d2
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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