Reaction #513145

ord-b716e0ad703b496ba1535b1168d1d4c9

Reaction equation

O=C1CCCCC1
Cyclohexanone
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
COC(=O)c1cc(Cl)ccc1N
methyl 2-amino-5-chlorobenzoate
→
COC(=O)c1cc(Cl)ccc1NC1CCCCC1
methyl 5-chloro-2-(cyclohexylamino)benzoate

Reactants

O=C1CCCCC1
Cyclohexanone
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
COC(=O)c1cc(Cl)ccc1N
methyl 2-amino-5-chlorobenzoate

Reagents

None

Solvents

CC(=O)O.ClCCCl
1,2-dichloroethane acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONBy post-treating
  2. 2
    Otherthe reaction liquid

Procedure

Cyclohexanone and sodium triacetoxyborohydride were added to a 1,2-dichloroethane-acetic acid solution of methyl 2-amino-5-chlorobenzoate, followed by stirring at room temperature. By post-treating the reaction liquid, methyl 5-chloro-2-(cyclohexylamino)benzoate was obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08106190B2uspto-grants-2012_01