Dimethylformamide → 4-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl ester

HRID 1750187Notes

Reaction equation

HRID 1750187 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.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[NH2:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29]>O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 120193-PentanamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 859985714-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl esterYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.38 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 25 ml of abs. DMF was added 5.60 g of potassium carbonate, followed by 2.67 g of 3-aminopentane. After 3 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 7.01 g (97%) of 4-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl ester as a light brown oil.

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-28cab29705574f309b5b540fffd17716
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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