Methyl 3-nitronaphthalene-1-carboxylate → Methyl 3-aminonaphthalene-1-carboxylate

HRID 1010616Notes

Reaction equation

HRID 1010616 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pd].C(O)C.ClCCl>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 1

HCID 260948Methyl 3-nitronaphthalene-1-carboxylate

Product 1

HCID 23423661Methyl 3-aminonaphthalene-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 1.15 g (1.08 mmol) of 10% palladium on carbon was added a suspension of 11.6 g (50.0 mmol) of the above methyl 3-nitro-1-naphthoate in 150 mL of anhydrous ethanol and 40 mL of anhydrous dichloromethane. The resulting suspension was agitated under an atmosphere of hydrogen at 40 psi for 3 h during which time all solids dissolved. The reaction mixture was filtered through a plug of Celite®, which was subsequently washed with dichloromethane (300 mL). The combined filtrates were concentrated in vacuo to yield the title compound as a pale green gum which was used without further purification. LC/MS 202.1 (M+1).

Workup

  1. dissolutiondissolved
  2. filtrationThe reaction mixture was filtered through a plug of Celite®, which
  3. washwas subsequently washed with dichloromethane (300 mL)
  4. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-a6ef63a589a340cd8bc6daaf0a29d7bc
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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