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

HRID 887463Notes

Reaction equation

HRID 887463 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-78dc0506cd9f44b494756e64eadffb18
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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