HCID 43390057, compound → HCID 43345830, compound

HRID 1190182Notes

Reaction equation

HRID 1190182 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1>CCO.CCOC(C)=O.[Pd]>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])=[O:17])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 43390057HCID 43390057, compound

Product 1

HCID 43345830HCID 43345830, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A slurry of N-(3-hydroxy-propyl)-2-(4-nitro-phenyl)-acetamide (as prepared in the previous step, 183 mg, 0.768 mmol) and 5% Pd—C (130 mg) in EtOH-EtOAc (5 mL, 4:1 v/v) was stirred under 1 atm H2 for 2 h. The reaction was filtered and concentrated to afford 152 mg (95%) of the title compound. 1H-NMR (DMSO-d6; 400 MHz): δ 7.78 (br s, 1H), 6.88 (d, 2H, J=8.3 Hz), 6.47 (d, 2H, J=8.3 Hz), 4.88 (br s, 2H), 4.39 (t, 1H, J=5.2 Hz), 3.43-3.34 (m, 2H), 3.16 (s, 2H), 3.08-3.03 (m, 2H), 1.55-1.48 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a2d43468bbf747f39a39bda148b835eb
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…