3-Azido-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol → 3-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 975928Notes

Reaction equation

HRID 975928 reaction equation
[N:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[CH2:6][CH:5]1[OH:16])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[CH2:6][CH:5]1[OH:16]

Participants

4

Reactant 1

HCID 151310693-Azido-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 151310713-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-olYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-azido-5 -methoxy-1,2,3,4-tetrahydronaphthalen-2-ol (1.8 g, 8.0 mmol) in 150 ml of MeOH was stirred with 10% Pd/C (20 mg) under H2 (18 psi) for 4 h. The reaction mixture was filtered and concentrated in vacuo to provide 1.4 g (91%) of the desired product as a colorless oil which was used in the next reaction without purification. 1H NMR (300 MHz, CDCl3 ): δ 2.0 (broad s, 2H), 2.24 (dd, 1H, J=10.4, 16.8 Hz), 2.84 (m, 2H), 3.16 (m, 2H), 3.59 (m, 1H), 3.78 (s, 3H), 6.66 (m, 2H), 7.09 (t, 1H, J=7.9 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d38333847ba74861872190b839e513d2
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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