4-Nitroaniline → HCID 69202260, compound

HRID 1394117Notes

Reaction equation

HRID 1394117 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)=O)[CH3:2].[N+:16]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([O-:18])=[O:17].Cl.[N+]([C:30]1C=CC(N)=C[CH:31]=1)([O-])=O>C(O)CCC>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[CH2:2][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 851564-Nitrobenzenamine hydrochlorideHCID 2063904Ethyl 3-(3-fluorophenyl)-3-oxopropanoate

Product 1

HCID 69202260HCID 69202260, compoundYield 434.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
118 °C

Procedure

Into a dry 2 L round-bottom flask was placed 106.3 grams (0.506 moles) of 3-(3-fluorophenyl)-3-oxo-propionic acid ethyl ester, 63.0 grams (0.456 moles) of 4-nitro-aniline and 4.0 grams (0.023 moles) of 4-nitro-aniline hydrochloride. To the mixture was added 1.3 L of n-butanol, the flask was fitted with a Soxhlet extractor (cup volume of 0.3 L), condenser and nitrogen inlet. Dry, activated 4 Å sieves (200 grams) were placed in the extractor cup and the reaction mixture heated to reflux temperature of 118° C. under nitrogen and maintained at that temperature for 90 hours. The reaction mixture was decanted while hot from a small amount of solids and chilled to −15° C. for 48 hours Crystalline solids were collected by vacuum filtration. The crystals were washed with 0.2 L of cold ethanol and two 0.2 L portions of hexanes and vacuum dried at 50° C. overnight to yield 35.8 grams (20.8% yield) of the title compound.

Workup

  1. customInto a dry 2 L round-bottom flask was placed
  2. customthe flask was fitted with a Soxhlet extractor (cup volume of 0.3 L), condenser and nitrogen inlet
  3. customDry
  4. temperaturethe reaction mixture heated
  5. temperaturemaintained at that temperature for 90 hours
  6. customThe reaction mixture was decanted while hot from a small amount of solids
  7. temperaturechilled to −15° C. for 48 hours Crystalline solids
  8. filtrationwere collected by vacuum filtration
  9. washThe crystals were washed with 0.2 L of cold ethanol and two 0.2 L portions of hexanes and vacuum
  10. customdried at 50° C. overnight

Sources & evidence

ORD record
ord-64036b15394d4b4da4463e012608b63a
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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