Acetic Acid → HCID 58160238, compound

HRID 1879568Notes

Reaction equation

HRID 1879568 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH2:25][OH:26])[C:14]3[C:19]([C:20]=2[CH:21]=1)=[CH:18][C:17]([N:22]([CH3:24])[CH3:23])=[CH:16][CH:15]=3)C1C=CC=CC=1.[C:27](O)(=O)C>CO.[Pd]>[CH3:23][N:22]([CH3:24])[C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:25][O:26][CH3:27])[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:21][C:20]2=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66934083HCID 66934083, compound

Product 1

HCID 58160238HCID 58160238, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [3-(benzyloxy)-6-(dimethylamino)-9H-carbazol-9-yl]methanol 7 (120 mg), Pd/C (100 mg) and acetic acid (cat. amount) in MeOH (15 mL) was hydrogenated at room temperature for 4 hrs. It was filtered through a short Celite pad. The filtrate was concentrated in vacuo to give the desired product (94 mg, 100%). NMR (acetone-d6, 400 MHz) δ: 7.38-7.50 (m, 4H), 7.05 (dd, J=8.8, 2.4 Hz, 1H), 6.97 (dd, J=8.4, 2.4 Hz, 1H), 5.62 (s, 2H), 3.20 (s, 3H), 2.94 (s, 6H). MS: m/z=271 (M+H+)+.

Workup

  1. filtrationIt was filtered through a short Celite pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-004a0d8c432d4f5eb4f554c553c5da30
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

Loading…