Potassium Carbonate → HCID 69217273, compound

HRID 1292853Notes

Reaction equation

HRID 1292853 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-0d37c261cd944813a246cd1220ef3e11
Source dataset
uspto-grants-2007_07
Patent number
US07238698B2

Reaction notes

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