HCID 19968570, compound → HCID 20222960, compound

HRID 975924Notes

Reaction equation

HRID 975924 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-])=O)=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]#[N:14])[CH2:8][CH2:7][CH2:6]2>CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([NH2:15])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]#[N:14])[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 19968570HCID 19968570, compound

Product 1

HCID 20222960HCID 20222960, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-5-nitro-l,2,3,4-tetrahydronaphthalene-1-carbonitrile (0.42 g, 1.8 mmol) and catalytic amount of 10% Pd/C in 100 ml of MeOH was stirred under H2 for 12 h at 25° C. The reaction mixture was filtered and concentrated in vacuo to yield the desired product as a colorless oil (0.36 g, >95%). 1H NMR (300 MHz, CDCl3): δ 1.93 (m, 4H), 2.48 (qt, 2H, J=5.7 Hz), 3.79 (s, 3H), 3.99 (t, 1H, J=6.3 Hz), 6.68 (dd, 2H, J=8.0, 8.9 Hz).

Workup

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

Sources & evidence

ORD record
ord-55de0cefb7944dcea4c0fa4123e786df
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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