8-Amino-2-naphthalenol → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1803748Notes

Reaction equation

HRID 1803748 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.[OH-].[Na+]>[Ni].C(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 83588-Amino-2-naphthalenolHCID 14798Sodium Hydroxide

Product 1

HCID 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A hydrogenation reaction vessel was charged with 8-aminonaphthalen-2-ol (Aldrich, 5.0 g, 31.4 mmol), 50% w/w sodium hydroxide (0.2 g, 2.5 mmol) and Raney nickel (slurry in water, 40% weight load, 2.0 g) in ethanol (100 mL). The vessel was purged with hydrogen gas several times before sealing under a hydrogen atmosphere at a pressure of 1300 psi followed by heating to 85° C. After 6 hours the mixture was filtered, and the filtrate was concentrated under reduced pressure to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.44-1.68 (m, 1H), 1.79-1.94 (m, 1H), 2.20 (dd, J=16.48, 7.63 Hz, 1H), 2.56-2.85 (m, 3H), 3.85-3.99 (m, 1H), 4.63 (s, 2H), 4.75 (d, J=4.12 Hz, 1H), 6.30 (d, J=7.48 Hz, 1H), 6.44 (d, J=7.78 Hz, 1H), 6.78 (t, J=7.63 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ ppm 27.35, 31.41, 33.36, 65.81, 111.35, 116.48, 119.13, 125.53, 136.00, 146.12. MS (DCI) m/z 164.06 (M+H)+.

Workup

  1. customA hydrogenation reaction vessel
  2. customThe vessel was purged with hydrogen gas several times
  3. filtrationAfter 6 hours the mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45fd200485d14769a66d9431d96741b5
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

Loading…