HCID 24744244, compound → 4-(dibenzo[b,d]furan-4-yl)aniline

HRID 735897Notes

Reaction equation

HRID 735897 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]3[O:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[CH:13]1[C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 24744244HCID 24744244, compound

Product 1

HCID 585107654-(dibenzo[b,d]furan-4-yl)anilineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-nitrophenyl)dibenzo[b,d]furan (22 g) in EtOAc (800 mL) was hydrogenated in presence of Pd/C (10%, 4.2 g) for 12 h at rt under 2 Kg of pressure. The reaction mixture was filtered, and the filtrates were concentrated. The residue was crystallized from chloroform/PetEther (6/4) to give the title compound (16 g, 84%) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.15 (d, 1H, J=7.6 Hz), 7.97 (d, 1H, J=7.6 Hz), 7.72 (d, 1H, J=8.1 Hz), 7.65 (d, 2H, J=8.4 Hz), 7.57 (d, 1H, J=8.6 Hz), 7.50 (m, 1H), 7.38 (m, 2H), 6.72 (d, 2H, J=8.4 Hz), 7.35 (s, 2H). M+(LC/MS(ESI)): 260.2

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrates were concentrated
  3. customThe residue was crystallized from chloroform/PetEther (6/4)

Sources & evidence

ORD record
ord-002d9846f3fb41b6a3e5ff905184c54c
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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