4-Nitroaniline → HCID 69202260, compound

HRID 2414762Notes

Reaction equation

HRID 2414762 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 20.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
118 °C

Procedure

3-(3-Fluorophenyl)-3-oxo-propionic acid ethyl ester, 106.3 grams (0.506 moles), 4-nitro-aniline, 63.0 grams (0.456 moles), and 4-nitro-aniline hydrochloride 4.0 grams (0.023 moles) were placed in a dry 2 L round-bottom flask. 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 at 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. customthe flask was fitted with a Soxhlet extractor (cup volume of 0.3 L), condenser and nitrogen inlet
  2. customDry
  3. temperaturethe reaction mixture heated
  4. temperaturemaintained at that temperature for 90 hours
  5. customThe reaction mixture was decanted while hot from a small amount of solids
  6. temperaturechilled to −15° C. for 48 hours Crystalline solids
  7. filtrationwere collected by vacuum filtration
  8. washThe crystals were washed with 0.2 L of cold ethanol and two 0.2 L portions of hexanes and vacuum
  9. customdried at 50° C. overnight

Sources & evidence

ORD record
ord-81cb8f7f8f6a4122ae8e19113514e362
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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