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

HRID 17056

반응식

HRID 17056 반응식
[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+]>C1COCC1>[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.8 g, 8.0 mmol) (Step A, Example 23) in THF (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).

후처리

  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

출처 및 근거

ORD 기록
ord-009bab1fa48d47b3b7eba0601a942247
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737295B2

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