2,6-Dichloro-4-(trifluoromethyl)nicotinamide → 2,6-Dichloro-4-(trifluoromethyl)nicotinic acid

HRID 1839356

반응식

HRID 1839356 반응식
N([O-])=[O:2].[Na+].[Cl:5][C:6]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([C:16]([F:19])([F:18])[F:17])[C:7]=1[C:8](N)=[O:9]>O.OS(O)(=O)=O>[Cl:5][C:6]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([C:16]([F:19])([F:18])[F:17])[C:7]=1[C:8]([OH:2])=[O:9]

참가 물질

5

반응물 2

HCID 27368742,6-Dichloro-4-(trifluoromethyl)nicotinamideHCID 23668193Sodium Nitrite

생성물 1

HCID 219481962,6-Dichloro-4-(trifluoromethyl)nicotinic acid수율 95%

시약·촉매·용매 2

HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

A solution of NaNO2 (9.59 g, 139 mmol) in water (95 mL) was added slowly to a solution of commercially available (Oakwood) 2,6-dichloro-4-(trifluoromethyl)nicotinamide (20.0 g, 77 mmol) in conc. H2SO4 resulting in evolution of heat and brown gas. The mixture was stirred at room temperature for 15 min, and then heated to 60° C. for 18 h. The solution was cooled to 0° C. and then water (15 mL) was added. The resulting mixture was extracted with Et2O (3×) and the combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was triturated with hexanes and vacuum-filtered to afford 2,6-dichloro-4-(trifluoromethyl)nicotinic acid (19 g, 95%) as an off-white solid: Rf=0.30 (9:1 CH2Cl2:MeOH), 1H-NMR (d6-DMSO, 300 MHz) 8 8.18 (s, 1H).

후처리

  1. temperatureof heat
  2. temperatureheated to 60° C. for 18 h
  3. temperatureThe solution was cooled to 0° C.
  4. extractionThe resulting mixture was extracted with Et2O (3×)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexanes
  8. filtrationvacuum-filtered

출처 및 근거

ORD 기록
ord-7fd96a09cf6f45e3b8c6cd2629125492
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677352B1

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