HCID 18696619, compound → 7-Methoxynaphthalen-1-amine

HRID 1870547Notes

Reaction equation

HRID 1870547 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[NH:13]CC2C=CC=CC=2)=[CH:5][CH:4]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[NH2:13])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 18696619HCID 18696619, compound

Product 1

HCID 2358177-Methoxynaphthalen-1-amineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7583Diphenyl EtherSolvent

Procedure

To a solution of crude title compound of Step A (42.1 g) in diphenyl ether (320 mL) was added 10% palladium on carbon (17.8 g). The heterogeneous black mixture was heated at reflux for 5 h under N2 while stirring. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was acidified with concentrated HCl and the resulting white precipitate was collected by filtration, washed with CH2Cl2, dissolved in water and treated with 50% aqueous NaOH until basic. The aqueous mixture was then extracted four times with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered and the filtrate was concentrated under reduced pressure to give 20.9 g of the title compound of Step B as a pink solid melting at 79-80° C. 1H NMR (CDCl3): δ 7.70 (d,1H), 7.29-7.13 (m,3H), 7.07 (d,1H), 6.80 (dd,1H), 4.0 (br s,2H), 3.94 (s,3H).

Workup

  1. temperatureThe heterogeneous black mixture was heated
  2. temperatureat reflux for 5 h under N2
  3. filtrationfiltered
  4. filtrationthe resulting white precipitate was collected by filtration
  5. washwashed with CH2Cl2
  6. dissolutiondissolved in water
  7. additiontreated with 50% aqueous NaOH until basic
  8. extractionThe aqueous mixture was then extracted four times with CH2Cl2
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d49207345eab47b790903df2e9cc02bb
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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