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

HRID 2183763

反応式

HRID 2183763 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒

実験手順

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) δ 8.18 (s, 1H).

後処理

  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

出典と根拠

ORDレコード
ord-32e15aa4fbef4ef4aa4e9f4b3835758b
出典データセット
uspto-grants-2005_05
特許番号
US06900205B2

関連ノート

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