Formic Acid → 2-(7-fluoro-1H-benzimidazol-1-yl)ethanol

HRID 603110Notes

Reaction equation

HRID 603110 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH2:12][CH2:13][OH:14].[CH:15](O)=O>[Pd]>[F:1][C:2]1[C:3]2[N:11]([CH2:12][CH2:13][OH:14])[CH:15]=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 284Formic Acid2×HCID 114241932-[(2-Fluoro-6-nitrophenyl)amino]ethanol

Product 1

HCID 113897452-(7-fluoro-1H-benzimidazol-1-yl)ethanolYield 64%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-[(2-fluoro-6-nitrophenyl)amino]ethanol (18.3 g, 91.5 mmol) dissolved in 90 mL of formic acid is added to a suspension of Pd—C 10% (300 mg) in 10 ml of formic acid. The mixture is shaken in a Parr apparatus under atmospheric pressure of H2 overnight. The reaction mixture is filtered over Celite, the solvent is evaporated under vacuum and the resulting residue dissolved in NH3 2M in ethanol. This solution is stirred at room temperature for 1 h (to cleave the formic acid adduct). A precipitate forms. This mixture is evaporated to dryness and purified by column chromatography (SiO2, DCM/MeOH 10:1 to 5:1), giving the desired product as a white solid (10.5 g, 64%) TLC: DCM/MeOH 5:1, Rf=0.23.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. customthe solvent is evaporated under vacuum
  3. dissolutionthe resulting residue dissolved in NH3 2M in ethanol
  4. stirringThis solution is stirred at room temperature for 1 h (
  5. customThis mixture is evaporated to dryness
  6. custompurified by column chromatography (SiO2, DCM/MeOH 10:1 to 5:1)

Sources & evidence

ORD record
ord-e4c33f80bee24186a11353118b09e35e
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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