4-Chlorobenzaldehyde → HCID 67230285, compound

HRID 386481Notes

Reaction equation

HRID 386481 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:14])=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:7]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:14])=[C:6]([N:8]3[CH2:12][CH2:11][CH2:10][C:9]3=[O:13])[CH:7]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 167718851-(5-Amino-2-fluorophenyl)-2-pyrrolidinone

Product 1

HCID 67230285HCID 67230285, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(5-amino-2-fluoro-phenyl)-pyrrolidin-2-one (0.34 g, 1.8 mmol), 4-chlorobenzaldehyde (0.25 g, 1.8 mmol) and sodium triacetoxyborohydride (0.75 g 3.6 mmol) was stirred in dry dichloromethane (25 ml) overnight. The reaction was quenched with water (25 ml) and the dichloromethane layer separated, dried (magnesium sulphate) and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2) eluting with ethyl acetate/dichloromethane (1:10) to afford the title compound as a yellow oil (253 mg, 44%). HPLC retention time 4.4 min, Mass spectrum (ES+) m/z 319 (M+H).

Workup

  1. customThe reaction was quenched with water (25 ml)
  2. customthe dichloromethane layer separated
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2)
  6. washeluting with ethyl acetate/dichloromethane (1:10)

Sources & evidence

ORD record
ord-274504934bfd4e96aa26c34146dfd17d
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

Loading…