Diethyl Ether → (3-Aminophenyl)(3,4,5-trimethoxyphenyl)methanone

HRID 892802Notes

Reaction equation

HRID 892802 reaction equation
C(C([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:9]=1)=O)(C)(C)C.Cl.C(O)(=O)C.C(OCC)C>C(O)(=O)C>[CH3:26][O:25][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[O:23][CH3:24])[C:14]([C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH2:7])=[O:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 19876863HCID 19876863, compoundHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 11748175(3-Aminophenyl)(3,4,5-trimethoxyphenyl)methanoneYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-tert-butylcarbonyl-3-(3,4,5-trimethoxybenzoyl)aniline (7.10 g, 18.92 mmol), prepared as described above, was dissolved in acetic acid (125 mL, 1.4N) at room temperature. A solution of hydrochloric acid/acetic acid (20 mL) was added and the mixture allowed to stand for 45 minutes. Diethylether (800 mL) was added and the resulting precipitate filtered and dried to yield 3-(3,4,5-trimethoxybenzoyl)aniline (5.24 g, 85.7%) as a tan solid.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-5fa3c52d799f45c1b1d4d626f476b739
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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