D-Psicose → Benzo[b]thiophene-6-methanamine, 2,3-dihydro-, 1,1-dioxide

HRID 1845127Notes

Reaction equation

HRID 1845127 reaction equation
[O:1]=[S:2]1(=[O:13])[CH:6]=[CH:5][C:4]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:3]1=2.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[OH-].[Pd+2].[OH-].C(O)C>[O:1]=[S:2]1(=[O:13])[CH2:6][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([CH2:11][NH2:12])=[CH:10][C:3]1=2

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 58187944HCID 58187944, compound

Product 1

HCID 58188230Benzo[b]thiophene-6-methanamine, 2,3-dihydro-, 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A hydrogenation par vessel was charged with 1,1-dioxo-1H-benzo[b]thiophene-6-carbonitrile (0.30 g, 1.57 mmol), ethanol (25 mL) and palladium hydroxide (66 mg). The vessel was put on a shaker under hydrogen at 40 Psi for 5 h. The reaction mixture was filtered through Celite and the filter cake was washed with methanol. The filtrate was concentrated to get the product as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-12d0c5e136ba4114bc28843a2ccde499
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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