Methyl 4-Amino-2-chlorobenzoate → 2-Chloro-4-hydroxy-benzoic acid methyl ester

HRID 1363413Notes

Reaction equation

HRID 1363413 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[Cl:11].N([O-])=[O:14].[Na+]>OS(O)(=O)=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:14])=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 2

HCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Compound of example 162 (7.9 g, 42.5 mmol) suspended in 10% aqueous H2SO4 (80 mL) was reacted with NaNO2 (3.5 g, 52.1 mmol in 35 mL water) as described in example 174. It was treated with a solution of CuSO4.5H2O (128 g, 513 mmol) and Cu2O (5.5 g, 38.4 mmol) in water (800 mL) as described in the same procedure to obtain the title compound.

Sources & evidence

ORD record
ord-5ee5b21741b248929c2d38fe98afedc2
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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