2-Chloro-4-nitroaniline → HCID 3400859, compound

HRID 602499Notes

Reaction equation

HRID 602499 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(#N)C>[CH2:16]([O:15][C:13](=[O:14])[NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[Cl:1])[CH3:17]

Participants

4

Reactant 2

HCID 84922-Chloro-4-nitroanilineHCID 10928Ethyl chloroformate2×

Product 1

HCID 3400859HCID 3400859, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of MgO (2.0 g), 2-chloro-4-nitroaniline (3.768 g, 21.83 mmol) and ethyl chloroformate (5 mL) in acetonitrile (25 mL) was heated to reflux temperature for 4 hours followed by addition of more ethyl chloroformate (4 mL). The heating was continued until full conversion (20 hours) then the reaction mixture was filtered via a plug of SiO2 (5 g) with ethyl acetate as an eluent. Evaporation in vacuo (50° C.) gave 5.8 g (100% yield) of crude title compound which was used in the next step without further purification. LC/MS (m/z) 245 ([M+H]+); RT=2.95, (UV, ELSD) 96%, 98.5%. 1H NMR (DMSO-d6): 1.27 (t, 3H), 4.19 (q, 2H), 8.06 (d, 1H), 8.19 (dd, 1H), 8.30 (d, 1H), 9.49 (s, NH).

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 4 hours
  3. customwas continued until full conversion (20 hours)
  4. filtrationthe reaction mixture was filtered via a plug of SiO2 (5 g) with ethyl acetate as an eluent
  5. customEvaporation in vacuo (50° C.)

Sources & evidence

ORD record
ord-06b1105738e243c6a3197b497761d225
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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