Ethyl 8-nitro-2-naphthoate → Ethyl 8-Amino-2-naphthoate

HRID 1089573Notes

Reaction equation

HRID 1089573 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:9]2)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:9]2

Participants

4

Reactant 1

HCID 13368523Ethyl 8-nitro-2-naphthoate

Product 1

HCID 14696377Ethyl 8-Amino-2-naphthoateYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

According to the procedure of W. Adcock, et al. Aust. J. Chem. 18, 1351 (1965), a suspension of ethyl 8-nitro-2-naphthoate prepared according to Price, et al. J. Am. Chem. Soc. 74, 3652 (1952) (8.2 g, 0.033 mol) in ethanol (240 mL) was hydrogenated at 50 psi over 10% Pd/C (820 mg) for 4 hours. The mixture was filtered through Solka floc® and concentrated. Recrystallization of the residue from EtOH/H2O gave a yellow solid (5.2 g, 72%), m.p. 97°-98° C.

Workup

  1. customprepared
  2. filtrationThe mixture was filtered through Solka floc®
  3. concentrationconcentrated
  4. customRecrystallization of the residue from EtOH/H2O

Sources & evidence

ORD record
ord-ed31c02e88cf472392a36ace4584fdaa
Source dataset
uspto-grants-1990_10
Patent number
US04966975

Reaction notes

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