Hydrochloric Acid → 5,6,7,8-Tetrahydro-2-naphthylamine

HRID 260676

Reaction equation

HRID 260676 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-])=O.O.Cl>C(O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 384457-Nitro-1-tetralone2×

Product 1

HCID 751935,6,7,8-Tetrahydro-2-naphthylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

7-Nitrotetralone (Formula 10) is dissolved in a solvent, such as ethanol or methanol, preferably ethanol (about 4 L/mole). To this solution is added water (about 400 ml/mmol), concentrated HCl (about 95 ml/mmol) and 10% palladium on carbon (about 40 g/mmol). The reaction mixture is hydrogenated at a pressure of about 30-40 psi for a period of about 12 to 24 hours, preferably about 18 hours. When the reaction is substantially compete, 2-amino-5,6,7,8-tetrahydronaphthalene of Formula 11 is isolated and purified by conventional means, preferably by preparative TLC or flash column chromatography.

Sources & evidence

ORD record
ord-8533fa867e7e41408578eb71c7b7f960
Source dataset
uspto-grants-1996_06
Patent number
US05530005

Linked notes

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