Potassium Carbonate → HCID 69217273, compound

HRID 272585Notes

Reaction equation

HRID 272585 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:15](=[O:18])([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:2][CH:3]=[C:4]([O:18][C:15]2[CH:4]=[CH:3][CH:2]=[CH:11][CH:6]=2)[C:5]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 171018Methyl 5-chloro-2-nitrobenzoate

Product 1

HCID 69217273HCID 69217273, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 5-chloro-2-nitrobenzoate (1) is reacted with an appropriately-substituted phenol (2) and base such as potassium carbonate in a solvent such as NMP to form the corresponding phenoxy-2-nitro-benzoic acid methyl ester (3). Compound (3) is hydrolyzed upon treatment with basic solution such as NaOH in water/MeOH to provide benzoic acid (4). Benzoic acid (4) is treated with thionyl chloride in solvent such as DMF to provide an intermediate acid chloride, which upon treatment with NH4OH in solvent such as THF provides benzamide (5). The nitro-benzamide (5) can be hydrogenated in solvent such as EtOH to provide amino-benzamide (6).

Sources & evidence

ORD record
ord-8b17cc9a62864ec7bd42a11f485050b6
Source dataset
uspto-grants-2008_11
Patent number
US07456185B2

Reaction notes

Loading…