Cyclohexanone → Methyl 5-chloro-2-(cyclohexylamino)benzoate

HRID 425963Notes

Reaction equation

HRID 425963 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:22][C:23]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]>ClCCCl.C(O)(=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:23]([NH:22][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12329834Methyl 5-chloro-2-(cyclohexylamino)benzoate

Reagents, catalysts & solvents 1

HCID 22609668HCID 22609668, compoundSolvent

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.

Workup

  1. additionBy post-treating
  2. customthe reaction liquid

Sources & evidence

ORD record
ord-b716e0ad703b496ba1535b1168d1d4c9
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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