Hydrochloric Acid → 4-(2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

HRID 1750223Notes

Reaction equation

HRID 1750223 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH2:28].Cl>O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:28][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]2[CH3:21])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 234322-MethylcyclohexylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 867144344-(2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 20.0 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 100 ml of abs. DMF was added 27.8 g of potassium carbonate, followed by 12.5 g of 2-methylcyclohexylamine. After 16 h at rt, the mixture was poured into water, the pH was adjusted to 4 by the addition of 2 M aqueous hydrochloric acid, and the reaction mixture was extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over sodium sulphate and concentrated to yield 29.4 g (100%) of 4-(2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester. C15H20N2O4 (292.34), LCMS (method 7—1—1): Rt=1.85 min, m/z=293.25 [M+H]+

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate three times
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6467bc29ec64019be7ddb283a6d0682
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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