HCID 24899700, compound → HCID 24899701, compound

HRID 1819863Notes

Reaction equation

HRID 1819863 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C:11]2[CH:23]=[CH:22][C:14]3[O:15][C:16]4[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>[Ni].C(O)C>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C:11]2[CH:23]=[CH:22][C:14]3[O:15][C:16]4[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 24899700HCID 24899700, compound

Product 1

HCID 24899701HCID 24899701, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-nitro-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-benzamide (0.67 g, 2.0 mmol) and Raney nickel (-1 g wet weight) in ethanol (200 mL) was hydrogenated at 40 PSI on a Parr shaker overnight. The mixture was filtered through Celite® and the filtrate was concentrated. The crude solid was recrystallized from acetonitrile to give 4-amino-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-benzamide (0.16 g). Mp 207-208° C; Anal. Calcd. for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14; Found: C, 74.29; H, 5.74; N, 9.08.

Workup

  1. customwas hydrogenated at 40 PSI on a Parr shaker overnight
  2. filtrationThe mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated
  4. customThe crude solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0d42bf1bb4db4837a70bf21cdf840485
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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