Hydrochloric Acid → Methyl 8-(aminomethyl)naphthalene-2-carboxylate

HRID 376807Notes

Reaction equation

HRID 376807 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8]2)#[N:2].Cl>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14756562Methyl 8-cyano-2-naphthoate

Product 1

HCID 14731550Methyl 8-(aminomethyl)naphthalene-2-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Part B--A mixture of methyl 8-cyano-2-naphthoate (1.0 g, 0.0047 mol) in methanol (35 mL) with concentrated hydrochloric acid (0.69 mL) and palladium on carbon catalyst (0.20 g, 5% Pd/C) was shaken for 6 hours at ambient temperature under an atmosphere of hydrogen (50 psi). The reaction mixture was filtered over Celite@ and washed with methanol. The filtrate was evaporated to dryness under reduced pressure and the residue was triturated with hexane to give methyl 8-aminomethyl-2-naphthoate (0.76 g, 0.0035 mol, 75%) as an oil. 1H NMR (DMSO) d 8.75 (s, 1H), 8.5 (bs, 2H), 8.2-8.05 (m, 3H), 7.75-7.70 (m, 2H), 4.6 (s, 2H), 3.95 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered over Celite@
  2. washwashed with methanol
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-8d3eb2f1019e4dffb8dc7a21db9406a5
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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