Dimethylformamide → HCID 57636266, compound

HRID 1750216Notes

Reaction equation

HRID 1750216 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[N:16]([CH:18]=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:16][CH2:18][CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 57636266HCID 57636266, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 25.0 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 100 ml of abs. DMF was added 26.0 g of potassium carbonate, followed by 14.2 g of (cycloheylmethyl)amine. After 16 h at rt, the mixture was poured into water, and extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over sodium sulphate and concentrated to yield 36.7 g (100%) of 4-(Cyclohexylmethyl-amino)-3-nitro-benzoic acid methyl ester as an orange solid.

Workup

  1. extractionextracted 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-f19fe98073794f679d54289e901f2455
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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