Pyridine → HCID 19603251, compound

HRID 1604563Notes

Reaction equation

HRID 1604563 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([Cl:25])=[C:7]([C:21]([Cl:24])=[CH:22][CH:23]=1)[CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2.N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>ClCCl>[C:32]([NH:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([Cl:25])=[C:7]([C:21]([Cl:24])=[CH:22][CH:23]=1)[CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11783746HCID 11783746, compound

Product 1

HCID 19603251HCID 19603251, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-(2-aminoethoxy)-2,6-dichlorobenzyloxy]-2-methylquinoline (11 mg) in dichloromethane were added pyridine (3.46 g) and acetic anhydride (4.47 mg), and the mixture was stirred for 30 minutes. The reaction mixture concentrated, and the reside was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V) to give 8-[3-(2-acetamidoethoxy)-2,6-dichlorobenzyloxy]-2-methylquinoline (6 mg) as an amorphous powder.

Workup

  1. concentrationThe reaction mixture concentrated
  2. customthe reside was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V)

Sources & evidence

ORD record
ord-117dd157c83a4dd99ad192833bf3c133
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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