Aniline → HCID 9846371, compound

HRID 256632Notes

Reaction equation

HRID 256632 reaction equation
[C:1]([C:6]1[CH:22]=[C:21]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:10]=1[C:11](O)=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCCCCCC>ClCCl.C(OCC)(=O)C>[C:1]([C:6]1[CH:22]=[C:21]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:10]=1[C:11]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6115AnilineHCID 8900HeptaneHCID 65578Oxalyl chlorideHCID 19373446HCID 19373446, compound

Product 1

HCID 9846371HCID 9846371, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2,4-di-tert-pentylphenoxy)-5-hydroxybenzoic acid (3.3 g, 8.9 mmol) and oxalyl chloride (1.25 g, 9.8 mmol) in dichloromethane (75 mL) was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue triturated with toluene (25 mL) followed by distillation of the solvent. The crystalline residue was taken up in dichloromethane (80 mL) and aniline (1.66 g, 17.9 mmol) was added. The reaction mixture was allowed to stir at room temperature for 8 hours, then submitted to aqueous, acidic workup. Flash column chromatography on silica gel with 90:10 heptane:ethyl acetate yielded the addition product. Recrystallization from heptane/ethyl acetate yielded analytically pure product in 79% overall yield.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with toluene (25 mL)
  3. distillationfollowed by distillation of the solvent
  4. customRecrystallization from heptane/ethyl acetate
  5. customyielded analytically pure product in 79% overall yield

Sources & evidence

ORD record
ord-92a8b996f6a746c9a301dc6ca8e9d4e0
Source dataset
uspto-grants-1993_11
Patent number
US05258407

Reaction notes

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