Hydrochloric Acid → (3-Amino-5-(trifluoromethyl)phenyl)methanol

HRID 217500

Reaction equation

HRID 217500 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.Cl.O.O.Cl[Sn]Cl>C([O-])(O)=O.[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 53414333(3-Amino-5-(trifluoromethyl)phenyl)methanolYield 98.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.8 g, 8.0 mmol) (Step A, Example 23) in TIE (36 mL) was added concentrated HCl (18 mL) and SnCl2.2H2O (8.7 g, 38.8 mmol). The reaction was stirred at room temperature for 24 hours and then poured slowly into saturated NaHCO3 (250 mL). After neutralization was complete, the reaction was extracted with EtOAc (3×50 mL). The organic extracts were washed with brine (75 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded 1.5 g (quantitative) of [3-amino-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (50% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 6.98 (s, 1H), 6.84 (s, 1H), 6.81 (s, 1H), 4.65 (s, 2H), 3.87 (bs, 1H).

Workup

  1. extractionthe reaction was extracted with EtOAc (3×50 mL)
  2. washThe organic extracts were washed with brine (75 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-4c95f83a74ec44c88ac3c00fc654936e
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Linked notes

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