Acetonitrile → N-Methoxy-N-methyl-4-(2-quinolin-2-yl-ethyl)-benzamide

HRID 1170305Notes

Reaction equation

HRID 1170305 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.C(#N)C.Cl.[CH3:26][O:27][NH:28][CH3:29].[OH-].[Na+]>O1CCOCC1.C(N(CC)CC)C>[CH3:26][O:27][N:28]([CH3:29])[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 685763074-(2-Quinolin-2-yl-ethyl)-benzoic acid

Product 1

HCID 86249320N-Methoxy-N-methyl-4-(2-quinolin-2-yl-ethyl)-benzamideYield 88%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(2-Quinolin-2-yl-ethyl)-benzoic acid (530 mg) in dioxane 5 ml/acetonitrile 5 ml was added triethylamine (0.60 ml) and O,N-Dimethyl-hydroxylamine hydrogen chloride (240 mg). After 72 h, the reaction mixture was poured into 1N sodium hydroxide solution and extracted with chloroform, dried magnesium sulfate, filtered and concentrated. Biotage MPLC chromatography eluting with 20-50% ethyl acetate provided the title compound (516 mg, 88%). MS: (M+H m/z=321.1).

Workup

  1. extractionextracted with chloroform, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washBiotage MPLC chromatography eluting with 20-50% ethyl acetate

Sources & evidence

ORD record
ord-ef16ca9a67464b3398c638abe54d72fa
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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