Trans-3-azido-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol → Trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol

HRID 542174Notes

Reaction equation

HRID 542174 reaction equation
[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[CH2:6][C@H:5]1[OH:16])=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[CH2:6][C@H:5]1[OH:16]

Participants

5

Reactant 2

HCID 15131068Trans-3-azido-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinolHCID 178418361HCID 178418361, compound

Product 1

HCID 15131070Trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

4.0 g of palladium on charcoal (10%) are coated with 100 ml of ethanol. 8.76 g (0.040M) of trans-3-azido-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol are dissolved in 100 ml of ethanol, and the solution is added to the catalyst suspension. The mixture is subsequently hydrogenated at 20° at 1.2 bar hydrogen pressure. Every 10 minutes for 50 minutes, the reaction vessel is emptied and rinsed with hydrogen. The reaction mixture is then filtered through a G 4 Hyflo suction filter. The catalyst is washed with methylene chloride and the filtrate concentrated by evaporation. Trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol is obtained (m.p. 130°-132° after purification by column chromatography, silica gel, methylene chloride and 10% methanol).

Workup

  1. additionthe solution is added to the catalyst suspension
  2. washrinsed with hydrogen
  3. filtrationThe reaction mixture is then filtered through a G 4 Hyflo suction
  4. filtrationfilter
  5. washThe catalyst is washed with methylene chloride
  6. concentrationthe filtrate concentrated by evaporation

Sources & evidence

ORD record
ord-a202e9593dda435b8057a1d4cafd66ba
Source dataset
uspto-grants-1987_04
Patent number
US04656167

Reaction notes

Loading…