Ethyl Acetate → 6-Methoxy-2-(trifluoromethyl)pyridin-3-amine

HRID 1297287ノート

反応式

HRID 1297287 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([N+:13]([O-])=O)=[CH:5][CH:4]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[C:6]([NH2:13])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 282423586-Methoxy-3-nitro-2-(trifluoromethyl)pyridine

生成物 1

HCID 447547986-Methoxy-2-(trifluoromethyl)pyridin-3-amine収率 71%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a solution of 6-methoxy-3-nitro-2-(trifluoromethyl)pyridine (3.61 g) in 95% Ethyl alcohol (162 ml) was added tin(II) chloride dihydrate. It was heated to 70° C. for 3 hr. After it was cooled to room temperature, it was poured over ice water and adjusted to pH 11 with 2N NaOH. It was stirred well with ethyl acetate and filtered through celite. The organic phase was separated, washed with brine, dried (MgSO4), filtered and concentrated. The flash column chromatography (SiO2, 3˜8% EtOAc in heptane) gave the title compounds (2.20 g, 71%). 1H NMR (CDCl3) δ 3.81, 6.70, 7.05; 19F NMR (CDCl3) δ 65.73; IR (liq.) 2434 (w), 2389, 2272, 2229, 2174, 1488 (s), 1436 (s), 1426 (s), 1276 (s), 1170 (s), 1102 (s, b), 1050 (s), 1024 (s), 740 (s), 658 (s) cm−1 HRMS (ESI) calcd for C7H7N2OF3+H1 193.0589. found 193.0581. Anal. Calcd for C7H7F3N2O: C, 43.76; H, 3.67; N, 14.58; F, 29.66. Found: C, 43.61; H, 3.49; N, 14.49.

後処理

  1. temperatureAfter it was cooled to room temperature
  2. filtrationfiltered through celite
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fb126a3ec82b4487816b8326641a7222
出典データセット
uspto-grants-2007_07
特許番号
US07250418B2

反応ノート

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