Hydrochloric Acid → 3-Nitro-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester

HRID 1750240Notes

Reaction equation

HRID 1750240 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.CCN(C(C)C)C(C)C.[F:24][C:25]([F:34])([F:33])[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[NH2:32].Cl>O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:32][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]2[C:25]([F:24])([F:33])[F:34])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 162287722-(Trifluoromethyl)cyclohexan-1-amine

Product 1

HCID 867144483-Nitro-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl esterYield 101.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.92 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 15 ml of abs. DMF was added 0.84 ml of DIPEA, followed by 0.85 g of 2-(trifluoromethyl)cyclohexylamine. After 16 h at rt, the mixture was poured into water, the pH was adjusted to 4 by the addition of 1 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 1.62 g (100%) of 3-Nitro-4-(2-trifluoromethyl-cyclohexylamino)-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-105844411e0e4c65a603b69b2ab362e7
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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