(3-Aminophenyl)(3,4-dimethoxyphenyl)methanone → (4-Aminophenyl)(3,4-dimethoxyphenyl)methanone

HRID 1745364Notes

Reaction equation

HRID 1745364 reaction equation
COC1C=C(C=CC=1OC)C(C1C=CC=C(N)C=1)=O.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:25]([C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=1)=[O:26]>[Pd].C(OCC)(=O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:25]([C:27]1[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=1)=[O:26]

Participants

5

Reactant 2

HCID 10563087(3-Aminophenyl)(3,4-dimethoxyphenyl)methanoneHCID 13954267(3,4-Dimethoxyphenyl)(4-nitrophenyl)methanone

Product 1

HCID 11543424(4-Aminophenyl)(3,4-dimethoxyphenyl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dimethoxy-4′-aminobenzophenone was prepared analogously to 3,4-dimethoxy-3′-aminobenzophenone using 3,4-dimethoxy-4′-nitrobenzophenone (1 g, 3.5 mmol) and 0.1 g of 10% palladium on carbon catalyst in 110 mL of ethyl acetate. The crude product was purified by flash column chromatography (silica gel, 12% ethyl acetate/methylene chloride) to afford 0.32 g (36%) of the product as a yellow solid: mp 189–191° C.; 1H NMR (CDCl3) δ 7.80–7.62 (m, 2H); 7.45–7.29 (m, 2H), 6.96–6.80 (m, 1H), 6.75–6.61 (m, 2H), 4.14 (s, 2H), 3.95 (s, 3H), 3.93 (s, 3H); 13C NMR (CDCl3) δ 194.2, 152.2, 150.5, 148.8, 132.6, 131.3, 128.0, 124.3, 113.6, 112.3, 109.7, 56.0; Anal. Calcd for C15H15NO3. Theoretical: C, 70.02; H, 5.88; N, 5.44. Found: C, 69.95; H, 6.18; N, 5.13.

Workup

  1. customThe crude product was purified by flash column chromatography (silica gel, 12% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-df690e524e81420aaf99659e7dcb86dd
Source dataset
uspto-grants-2006_03
Patent number
US07019030B2

Reaction notes

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