Aniline → HCID 7923026, compound

HRID 1826802Notes

Reaction equation

HRID 1826802 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN1CCCC1.C(N(C(C)C)CC)(C)C>CCOC(C)=O>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 6115AnilineHCID 84541-MethylpyrrolidineHCID 81531DiisopropylethylamineHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 7923026HCID 7923026, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-5-nitrobenzonitrile (Aldrich) (3.64 grams (hereinafter “g”), 20 millimoles (hereinafter “mmol”), aniline (2 milliliter (hereinafter “mL”), 22 mmol), N-methylpyrollidine (10 mL) and diisopropylethylamine (4 mL) were combined and heated to 120° under Ar for 18 hours (hereinafter “h”), cooled, poured into EtOAc (150 mL), washed with H2O (3×50 mL) and saturated aqueous (hereinafter “satd. aq.) NaCl (50 mL), dried (Na2SO4), concentrated, and the residue was triturated with hexane, filtered and the solid was washed with hexane and dried in vacuo to afford 4.23 g (88%) of the title compound as a light green solid. 1H NMR (400) MHz, δ: 8.45 (finely split doublet, 1), 8.19 (dd, 1), 7.48 (m,3), 7.28 (d,2), 7.06 (d, 1), 6.96 (br s,1).

Workup

  1. temperatureheated to 120° under Ar for 18 hours (hereinafter “h”)
  2. temperaturecooled
  3. washwashed with H2O (3×50 mL)
  4. dry with materialaq.) NaCl (50 mL), dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue was triturated with hexane
  7. filtrationfiltered
  8. washthe solid was washed with hexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-e13988700a5649dc89b67f5ebc9bc068
Source dataset
uspto-grants-2006_05
Patent number
US07053098B1

Reaction notes

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