Hydrochloric Acid → 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

HRID 1750229Notes

Reaction equation

HRID 1750229 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+].Cl.[CH3:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[NH2:29].Cl>O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:29][C@@H:24]2[CH2:25][CH2:26][CH2:27][CH2:28][C@H:23]2[CH3:22])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 12714251(1R,2R)-2-methylcyclohexan-1-amine hydrochloride

Product 1

HCID 867144374-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.47 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 35 ml of abs. DMF was added 13.47 g of potassium carbonate, followed by 4.96 g of (1R,2R)-2-Methyl-cyclohexylamine-hydrochloride. After 1.5 h at 60° C., the mixture was poured into water, the pH was adjusted to 5-6 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 9.28 g (98%) of 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester.

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-2f8813387ba54ca8b6fcf2d57ac326f3
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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