Pyridine → HCID 22614844, compound

HRID 2270926Notes

Reaction equation

HRID 2270926 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[C:17]([Cl:18])=[C:16]([Cl:19])[CH:15]=[C:14]2[C:9]=1[N:10]=[C:11]([O:22][CH3:23])[C:12]([O:20][CH3:21])=[N:13]2.N1C=CC=CC=1>ClCCl>[Cl:18][C:17]1[C:8]([NH:7][C:4](=[O:5])[CH2:3][O:2][CH3:1])=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:19])[N:13]=[C:12]([O:20][CH3:21])[C:11]([O:22][CH3:23])=[N:10]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 106066205-Amino-6,7-dichloro-2,3-dimethoxyquinoxaline

Product 1

HCID 22614844HCID 22614844, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyacetylchloride (27.3 ml, 32.4 g, 0.30 mol) was added to a stirred mixture of 5-amino-6,7-dichloro-2,3-dimethoxyquinoxaline (Preparation 2) (73.8 g, 0.27 mol) and pyridine (26.4 ml, 25.89, 0.33 mol) in dichloromethane (1.2 liters) at room temperature under nitrogen. After 18 hours standing at room temperature, the mixture was washed with 2M aqueous hydrochloric acid solution followed by brine, then dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with methanol and filtered to give 6,7-dichloro-2,3-dimethoxy-5-methoxyacetamidoquinoxaline (82.09, 88%) as an off-white solid. mp 171-173° C.

Workup

  1. washthe mixture was washed with 2M aqueous hydrochloric acid solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ddef088435144642bcf4b7f7706c4c97
Source dataset
uspto-grants-2001_12
Patent number
US06333326B1

Reaction notes

Loading…