4-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene → 4-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

HRID 2184188Notes

Reaction equation

HRID 2184188 reaction equation
C([NH:5][C:6]1[C:7]([F:18])=[C:8]([CH2:15][CH2:16][OH:17])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1)(C)(C)C>Cl>[NH2:5][C:6]1[C:7]([F:18])=[C:8]([CH2:15][CH2:16][OH:17])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 224753164-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

Product 1

HCID 207922134-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzeneYield 93.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-{3-[(tert-butyl)amino]-2-fluoro-6-nitrophenyl}ethanol (3.9 g, 15 mmol), as prepared in the preceding step, in concentrated HCl (40 mL) was refluxed for 2 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (6×50 mL). The extracts were combined, washed with saturated NaHCO3 (2 times) and brine, dried over Na2SO4, and concentrated to give the crude product as a solid. The solid was triturated in hexane, filtered, and dried in high vacuum to produce the title compound (2.8 g, 93% yield) as a yellow solid. 1H-NMR (400 MHz, CD3OD) δ 7.80 (dd, J=9.1, 1.5 Hz, 1H), 6.70 (t, J=9.0 Hz, 1H), 3.77 (t, J=7.1 Hz, 2H), 3.26 (dt, J=7.3, 2.8 Hz, 2).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate (6×50 mL)
  3. washwashed with saturated NaHCO3 (2 times) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product as a solid
  7. customThe solid was triturated in hexane
  8. filtrationfiltered
  9. customdried in high vacuum

Sources & evidence

ORD record
ord-b34e9e69c527430a885cff6d7c7fb3b4
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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