Methanol → 3-Methyl-indan-1-ylamine

HRID 1397519Notes

Reaction equation

HRID 1397519 reaction equation
C[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[N:11]O.[CH3:13]O>[Pd]>[CH3:13][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([NH2:11])[CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 73454082Methylindan-1-one oxime

Product 1

HCID 227426043-Methyl-indan-1-ylamineYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of-methylindan-1-one oxime (223 mg, 1.38 mmol) and 10% palladium on carbon (14.7 mg, 50% water wet) in MeOH (5.00 mL) was stirred under an atmosphere of hydrogen overnight. The mixture was then filtered through celite, washed through with MeOH and the combined filtrates were concentrated in vacuo to afford the title compound (195 mg, 96%). 1H NMR (CDCl3, 300 MHz) δ: 7.39-7.14 (m, 4H), 4.26 (dd, J=7.2, 9.4 Hz, 1H), 3.13-2.96 (m, 1H), 2.71 (ddd, J=6.9, 6.9, 12.5 Hz, 1H), 1.75 (bs, 2H), 1.35 (d, J=6.8 Hz, 3H), 1.25 (ddd, =9.9, 9.9, 11.7 Hz, 1H) ppm.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashed through with MeOH
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-859be4cb240648ec811f481b3791fe8e
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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