HCID 68089435, compound → HCID 68103964, compound

HRID 1615676Notes

Reaction equation

HRID 1615676 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[N+:13]([O-])=O.[H][H]>CO.[Pd]>[CH3:1][NH:2][C:3]1[C:4]([NH2:13])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 68089435HCID 68089435, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68103964HCID 68103964, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-methyl-1-nitro-5,6,7,8-tetrahydronaphthalen-2-amine (crude product from the previous step, 190 mg, 0.918 mmol) in MeOH (20 mL) was added 10% Pd on carbon (98 mg, 0.0918 mmol) under nitrogen, then replaced with hydrogen atmosphere (1 L). The resulting mixture was stirred at room temperature for 16 h. After filtration through Celite, the filtrate was concentrated and the residue was purified by prep-TLC (DCM/MeOH v/v 10:1) to give N2-methyl-5,6,7,8-tetrahydronaphthalene-1,2-diamine as a white solid (100 mg, 61% yield). ESI MS: m/z 177 [M+H]+.

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by prep-TLC (DCM/MeOH v/v 10:1)

Sources & evidence

ORD record
ord-acff2e1647c1491c96dc07fe3b9732e8
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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