Hydrogen chloride-ethyl acetate → HCID 67509866, compound

HRID 623507Notes

Reaction equation

HRID 623507 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:15])([F:14])[F:13])[C:6]=1[F:16])=[N+]=[N-].C(OC(=O)C)C.[ClH:23]>[Pd].CO>[ClH:23].[F:16][C:6]1[C:7]([O:11][C:12]([F:14])([F:15])[F:13])=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][NH2:1]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131735181HCID 131735181, compound

Product 1

HCID 67509866HCID 67509866, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(azidomethyl)-2-fluoro-3-(trifluoromethoxy)benzene (0.81 g, 3.46 mmol, Step-3), palladium 10% on carbon (0.20 g), 4M hydrochloric acid ethyl acetate solution (4 mL), and methanol (20 mL) is stirred at room temperature under hydrogen atmosphere (1 atm). After filtration through a pad of celite, the filtrate is concentrated under reduced pressure. The residue is crystallized from ether and diisopropyl ether to give 0.85 g (>99% yield) of the title compound as a white solid.

Workup

  1. filtrationAfter filtration through a pad of celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is crystallized from ether and diisopropyl ether

Sources & evidence

ORD record
ord-b311239bf5e44488b763420d4788a296
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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