1,2-Dichloroethane → 4-Hydroxy-N-methoxy-N-methylbenzamide

HRID 2192003Notes

Reaction equation

HRID 2192003 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(C(C)C)C(C)C)C.C(Cl)CCl>CN(C=O)C.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:13]([O:14][CH3:15])[CH3:12])=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1354-Hydroxybenzoic AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 113897574-Hydroxy-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxybenzoic acid (20.29 g, 147 mmol), N,O-dimethylhydroxylamine hydrochloride (21.49 g, 220 mmol), N-ethyl-N-isopropylpropan-2-amine (77 mL, 441 mmol), hobt (22.50 g, 147 mmol), and EDC (33.8 g, 176 mmol) in DMF (100 mL) was stirred at RT in 24 h. H2O was added, extracted with ether (3×), dried over MgSO4, concentrated, and purified by ISCO (40% EtOAc/Hexanes) to give the titled compound. MS [M+1]: 182.1.

Workup

  1. extractionextracted with ether (3×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by ISCO (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-27fb31cf2cca48c7a4a891a5c951c378
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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