4-Chlorobenzylamine → HCID 22498719, compound

HRID 1814889Notes

Reaction equation

HRID 1814889 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]([O:10]CC)=O)[C:5](=[O:13])[C:4]2[CH:14]=[CH:15][O:16][C:3]1=2.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:8]([C:6]2[C:5](=[O:13])[C:4]3[CH:14]=[CH:15][O:16][C:3]=3[N:2]([CH3:1])[CH:7]=2)=[O:10])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 10236112HCID 10236112, compound

Product 1

HCID 22498719HCID 22498719, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxylate (Preparation 9, 1.00 g) and 4-chlorobenzylamine (5.5 mL) was heated to 190° C. for 1 h. The reaction mixture was allowed to cool for several minutes and toluene (50 mL) was added. The resulting off-white solid was filtered and recrystallized from ethyl acetate to yield 0.979 g (68%) of the title compound as a pale yellow solid. Physical characteristics. M.p. 197-205° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.62, 8.59, 7.92, 7.41-7.33, 7.06, 4.55, 3.94; 13C NMR (100 MHz, CDCl3) δ 174.0, 164.8, 153.4, 141.4, 140.5, 137.3, 132.8, 128.9, 128.7, 116.7, 114.2, 107.9, 42.6, 37.7; MS (ESI+) m/z 317 (M+H)+.

Workup

  1. temperatureto cool for several minutes
  2. filtrationThe resulting off-white solid was filtered
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-710a3cd8afb644639f9e4d7e1c34144a
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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