Aniline → 3-Nitro-phtalanilide

HRID 42736

Reaction equation

HRID 42736 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]([C:7]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:9])[C:5]=1[C:10]([NH:1][C:4]1[CH:14]=[CH:13][CH:12]=[CH:6][CH:5]=1)=[O:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 216313-Nitrophthalic anhydride

Product 1

HCID 130057913-Nitro-phtalanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

50 g (259 mmol) 3-nitro-phtalic anhydride and 24.7 g (24.1 mL, 266 mmol) aniline in 710 mL acetic acid were heated to reflux for 3 hours under an argon atmosphere. Acetic acid was removed under reduced pressure and the residue was treated with 150 mL ethanol at 0° C. The precipitated 3-nitro-phtalanilide was isolated by filtration, washed with a small amount of cold ethanol and dried. 59.1 g (58%) 3-nitro-phtalanilide was isolated (m.p. 139-141° C.)

Workup

  1. temperatureto reflux for 3 hours under an argon atmosphere
  2. customAcetic acid was removed under reduced pressure
  3. additionthe residue was treated with 150 mL ethanol at 0° C

Sources & evidence

ORD record
ord-cbcfd8e7cde14fd89b041b65432e7844
Source dataset
uspto-grants-2013_09
Patent number
US08536217B2

Linked notes

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