Methyl 4-((tert-butoxycarbonyl)amino)-2,6-dichlorobenzoate → Methyl 4-amino-2,6-dichlorobenzoate

HRID 449870Notes

Reaction equation

HRID 449870 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[C:17]([Cl:19])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:20])[CH:10]=1)=O)(C)(C)C>OS(O)(=O)=O.CCOC(C)=O>[NH2:8][C:9]1[CH:10]=[C:11]([Cl:20])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:17]([Cl:19])[CH:18]=1

Participants

3

Reactant 1

HCID 20610066Methyl 4-((tert-butoxycarbonyl)amino)-2,6-dichlorobenzoate

Product 1

HCID 51341879Methyl 4-amino-2,6-dichlorobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 86628183Ethyl acetate sulfuric acidSolvent

Procedure

A solution of methyl 4-(tert-butoxy carbonylamino)-2,6-dichlorobenzoate (65 g, 0.49 mol) in H2SO4/EtOAc (3 N, 20 mL) was stirred at room temperature for 2 hours. The reaction mixture was filtered, and the solid was collected to afford methyl 4-amino-2,6-dichlorobenzoate (60 g, yield: 92%). 1H NMR (DMSO-d6, 400 MHz) δ 8.40 (brs, 3H), 6.61 (s, 2H), 3.80 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solid was collected

Sources & evidence

ORD record
ord-bb69f6630e0b45ebb44fc9a1d6c46dec
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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