P-Anisidine → HCID 18174449, compound

HRID 395760Notes

Reaction equation

HRID 395760 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:14]=1[C:15](O)=[O:16])([O-:12])=[O:11].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:15](=[O:16])[C:14]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:13]=2[N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 183715-Methyl-2-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18174449HCID 18174449, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-methoxyaniline (1.4 g, 11 mmol) and 2-nitro-5-methylbenzoic acid (2.0 g, 11 mmol) in dimethylformamide (20 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.17 g, 16.5 mmol). After 12 h, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed twice with 1 M aqueous citric acid, once with water, twice with saturated aqueous sodium bicarbonate solution, once with water, and once with saturated aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with diethyl ether, filtered, and dried in vacuo to give 1.57 g (50%) of the title compound as a yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed twice with 1 M aqueous citric acid, once with water, twice with saturated aqueous sodium bicarbonate solution, once with water
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d73b026e7a5b45d4bbf70f39435f658d
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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