HCID 12484293, compound → 2-Aminotetralin

HRID 1656639Notes

Reaction equation

HRID 1656639 reaction equation
C(N[C:5]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:6]=1OCC1OC1)(=O)C>C(O)C.Cl.C1C2C(=CC=CC=2)CCC1NCC(O)COC1C=CC=C([N+]([O-])=O)C=1NC(=O)C>[NH2:16][CH:15]1[CH2:14][CH2:13][C:12]2[C:6](=[CH:15][CH:5]=[CH:6][CH:12]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 12484293HCID 12484293, compound

Product 1

HCID 346772-AminotetralinYield 202.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14751075HCID 14751075, compoundSolvent

Procedure

Following the procedure of Example 27, but starting from 1-(2-acetamido-3-nitrophenoxy)-2,3-epoxypropane (5 g) and 2-aminotetralin (2.96 g) in absolute ethanol (80 ml), N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-acetamido-3-nitrophenoxy)propanamine hydrochloride is obtained ((iA): R=H, E=acetamido, G=nitro, and the chain is attached to position 2 of the tetralin moiety) (Ex. 89). A mixture of N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-acetamido-3-nitrophenoxy)propanamine hydrochloride (4 g) and 97% formic acid (19 ml) is charged in a hydrogenation vessel and freezed. The air contained in the reaction vessel is replaced by nitrogen and 10% Pd/C (0.25 g) is rapidly introduced therein. Hydrogenation is carried out at room temperature and 2.5 bar until the theoretical amount of hydrogen has been consumed. The reaction mixture is then heated, at atmospheric pressure, for 2 hours by means of a boiling water-bath. The catalyst is filtered off, the filtrate is evaporated to dryness and the obtained residue is taken up in hydrogen chloride saturated-isopropanol.

Sources & evidence

ORD record
ord-e24e4bbd3bec43b2b7438ae5f1957939
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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