HCID 69057961, compound → 5-amino-N-benzylnaphthalene-1-carboxamide

HRID 1818069Notes

Reaction equation

HRID 1818069 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:20]2[C:15](=[C:16]([N+:21]([O-])=O)[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]2[C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

4

Reactant 1

HCID 69057961HCID 69057961, compound

Product 1

HCID 102147315-amino-N-benzylnaphthalene-1-carboxamideYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Palladium on carbon (14 mg) was added to a suspension of N-benzyl-5-nitronaphthalene-1-carboxamide (128.0 mg, 0.418 mmol) in methanol (2.5 ml). The mixture was stirred at room temperature for 2 hours, under hydrogen atmosphere. After the palladium on carbon was filtered off, the filtrate was concentrated. The residue was solidified by a mixture of isopropyl ether: ethyl acetate (1:1), and the resulting solid was washed with isopropyl ether and dried to give the title compound as a light yellow solid (102 mg, 88.7%).

Workup

  1. filtrationAfter the palladium on carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was solidified by a mixture of isopropyl ether: ethyl acetate (1:1)
  4. washthe resulting solid was washed with isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-25a9f81951214d0b860770bfa0811780
Source dataset
uspto-grants-2009_10
Patent number
US07598418B2

Reaction notes

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