Hydrochloric Acid → 4'-Nitrobenzanilide

HRID 1956458Notes

Reaction equation

HRID 1956458 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C1COCC1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 74754-NitroanilineHCID 11430Potassium Carbonate

Product 1

HCID 769304'-Nitrobenzanilide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitroaniline (4-7) (10.0 g, 72 mmol) and anhydrous potassium carbonate (20 g, 1.44 mmol) in anhydrous THF (240 mL) and benzoyl chloride (9.1 mL, 78 mmol) was stirred at RT overnight. The resultant solution was poured into 10% aq. HCl (200 mL) and cooled to 0° C. The yellow solid precipitated was filtered, washed successively with water (200 mL) and hexane (200 mL). Further drying under vacuum overnight provided the required 4-nitro-N-benzoylaniline.

Workup

  1. temperaturecooled to 0° C
  2. customThe yellow solid precipitated
  3. filtrationwas filtered
  4. washwashed successively with water (200 mL) and hexane (200 mL)
  5. customFurther drying under vacuum overnight

Sources & evidence

ORD record
ord-cf264334b7d8468eb9f999ed8afb38b7
Source dataset
uspto-grants-1998_07
Patent number
US05780480

Reaction notes

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