Ammonium Chloride → 2-(2,3-Dihydroxy-propylamino)-4-fluorobenzonitrile

HRID 900476Notes

Reaction equation

HRID 900476 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15].C(N(C(C)C)C(C)C)C.[NH4+].[Cl-]>CS(C)=O>[OH:16][CH:13]([CH2:14][OH:15])[CH2:12][NH:11][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735613-Amino-1,2-propanediolHCID 775452,4-DifluorobenzonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 669527352-(2,3-Dihydroxy-propylamino)-4-fluorobenzonitrileYield 41.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2,4-Difluoro-benzonitrile (1.39 g, 10 mmol), 3-amino-propane-1,2-diol (0.911 g, 10 mmol), and ethyl-diisopropyl-amine (1.74 mL) in DMSO (10 mL) was microwaved at 200° C. for 7 min. Then the reaction mixture was poured into a saturated NH4Cl aq. solution (100 mL), extracted with EtOAc (3×100 mL), dried over Na2SO4, filtered, concentrated. The crude mixture was purified by flash silica gel chromatography (EtOAc-Hexane 1:1) to give 2-(2,3-Dihydroxy-propylamino)-4-fluoro-benzonitrile (0.87 g, 41.4% yield). LCMS (m/z): M+H=211.

Workup

  1. customwas microwaved at 200° C. for 7 min
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified by flash silica gel chromatography (EtOAc-Hexane 1:1)

Sources & evidence

ORD record
ord-8469811cd4514ac08e838dcb28e36ca2
Source dataset
uspto-grants-2008_04
Patent number
US07358370B2

Reaction notes

Loading…