5-Chloro-2-methoxybenzoyl chloride → 1-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester

HRID 2379088Notes

Reaction equation

HRID 2379088 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH2:14])[CH:6]=1)=[O:4].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22]>ClCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH:14][C:21](=[O:22])[C:20]2[CH:24]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[O:25][CH3:26])[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 536914421-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.985 g, 5.0 mmol) was reacted with 5-chloro-2-methoxybenzoyl chloride (1.04 g, 5.1 mmol) in dichloromethane (25 ml) and pyridine (10 ml). After an aqueous work-up, purification via flash column chromotography (silica gel, 8% methanol/dichloromethane) gave the product, MP: 149°-150° C.

Workup

  1. customAfter an aqueous work-up, purification via flash column chromotography (silica gel, 8% methanol/dichloromethane)
  2. customgave the product, MP: 149°-150° C.

Sources & evidence

ORD record
ord-9df25bd9a8ef496db3ea87da5b5d647f
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

Loading…