4-Chloroaniline → HCID 11323731, compound

HRID 427710Notes

Reaction equation

HRID 427710 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[OH-].[Na+]>CCOC(C)=O>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[CH2:2][C:1]([OH:7])=[O:12])=[O:6])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 12801Homophthalic anhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 11323731HCID 11323731, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of homophthalic anhydride (4.0 g, 24.7 mmol) in 250 mL of CHCl3 was treated with 4-chloroaniline (3.31 g, 25.9 mmol). After 16 h, the mixture was poured into EtOAc and 1 N NaOH. The aqueous layer was washed with EtOAc, then brought to a pH of 2-3 by addition of 1 N HCl. The aqueous layer was washed with EtOAc (2×), and the combined extracts were dried (MgSO4) and concentrated. Recrystallization of the residue from EtOAc/hexanes yielded 3.41g (48%) of the title compound.

Workup

  1. washThe aqueous layer was washed with EtOAc
  2. additionbrought to a pH of 2-3 by addition of 1 N HCl
  3. washThe aqueous layer was washed with EtOAc (2×)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customRecrystallization of the residue from EtOAc/hexanes

Sources & evidence

ORD record
ord-62cd7f3d9ce44512a02ad7c92d56e4f9
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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