Acetic Anhydride → N-[1-(4-bromopyridin-2-yl)-4-methoxybutyl]acetamide

HRID 656233Notes

Reaction equation

HRID 656233 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH2:14])[CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:14][C:15](=[O:17])[CH3:16])[CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 686532511-(4-Bromopyridin-2-yl)-4-methoxybutylamine

Product 1

HCID 68652850N-[1-(4-bromopyridin-2-yl)-4-methoxybutyl]acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 32.0 g of 1-(4-bromopyridin-2-yl)-4-methoxybutylamine in 150 ml of glacial acetic acid is mixed with 37 ml of acetic anhydride. The reaction solution is stirred at 50° C. for 30 minutes and then diluted with ethyl acetate. It is basified with 2M sodium hydroxide solution, and the phases are separated. The aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are evaporated. The title compound is obtained as a yellowish solid from the residue by flash chromatography (SiO2 60 F). Rf=0.38 (EtOAc-methanol 9:1); Rt=2.33 (Gradient I).

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×)
  3. customThe combined organic phases are evaporated

Sources & evidence

ORD record
ord-216e598d7e3e4400a697266c81525bd9
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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