Aniline → HCID 10822558, compound

HRID 1875461Notes

Reaction equation

HRID 1875461 reaction equation
Cl.[F:2][C:3]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:4]=1[NH2:5].[OH-:11].[Na+].N[C:14]1[CH:19]=CC=CC=1.[CH2:20]1[O:22][CH2:21]1>CO.CC(O)=O>[OH:22][CH2:20][CH2:21][N:5]([CH2:14][CH2:19][OH:11])[C:4]1[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:3]=1[F:2]

Participants

7

Reactant 4

HCID 6115AnilineHCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 448869124-Amino-3-fluorophenol hydrochloride

Product 1

HCID 10822558HCID 10822558, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-4-hydroxyaniline hydrochloride (3 g) in MeOH (50 mL) was treated with aqueous NaOH (0.74 g in 10 mL deionized water) and the resulting clear solution was concentrated to dryness to provide a residue of crude aniline free base. A 0° C. solution of the crude aniline residue in 1:1 AcOH/deionized water (32 mL) in a pressure tube was treated with liquid ethylene oxide condensed at −78° C. (7.8 g), the tube was sealed, and the reaction mixture allowed to warm up to RT. The reaction mixture was stirred at RT 48 h then cooled, evaporated to dryness and purified by silica gel chromatography (0-7% MeOH/DCM) to provide N,N-bis-(2-hydroxyethyl)-2-fluoro-4-hydroxyaniline (2 g) as a grey powder.

Workup

  1. concentrationthe resulting clear solution was concentrated to dryness
  2. customto provide a residue of crude aniline free base
  3. customthe tube was sealed
  4. temperaturethen cooled
  5. customevaporated to dryness
  6. custompurified by silica gel chromatography (0-7% MeOH/DCM)

Sources & evidence

ORD record
ord-bd2d86c2ea0b4deaaf6b6ecc950dbbdc
Source dataset
uspto-grants-2012_11
Patent number
US08309554B2

Reaction notes

Loading…