4-Ethoxy-2-nitroaniline → HCID 10269566, compound

HRID 1007231Notes

Reaction equation

HRID 1007231 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]([OH:11])=O.[CH2:14]([O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1)[CH3:15].Cl.CN(C)CCCN=C=NCC>C1COCC1.CCCCCC.C(OCC)(=O)C>[F:12][C:2]([F:1])([F:13])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]([NH:21][C:20]1[CH:22]=[CH:23][C:17]([O:16][CH2:14][CH3:15])=[CH:18][C:19]=1[N+:24]([O-:26])=[O:25])=[O:11]

Participants

6

Reactant 3

HCID 692294-Ethoxy-2-nitroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

Product 1

HCID 10269566HCID 10269566, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-(trifluoromethyl)pyridine-3-carboxylic acid (100 mg, 0.52 mmol), 4-ethoxy-2-nitroaniline (94.7 mg, 0.52 mmol), and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (199.3 mg, 1.04 mmol) in THF (5 ml) was refluxed overnight. The mixture was cooled to room temperature, diluted with 100 ml of hexane:ethyl acetate (1:1), wash with 2 N NaOH (50 ml), water (50 ml), saturated aqueous NaCl (50 ml), dried over anhydrous sodium sulfate and evaporated. The crude product was purified by column chromatography using hexane:ethyl acetate (2:1) to give 17.3 mg (9.4% yield) of the title compound as yellow solid. 1H NMR (CDCl3): 10.48 (s, 1H), 9.01-8.96 (m, 2H), 8.74 (d, J=9.3 Hz, 1H), 7.74-7.69 (m, 2H), 7.32 (dd, J=3.0, 9.3 Hz, 1H), 4.13 (q, J=6.9 Hz, 2H), 1.48 (t, J=6.9 Hz, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. washwash with 2 N NaOH (50 ml), water (50 ml), saturated aqueous NaCl (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ea80749afc354ce1bf8420d211882225
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

Loading…