Acetic Anhydride → 4-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

HRID 930642ノート

反応式

HRID 930642 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:22])C>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:22])[CH:10]=2)=[CH:5][CH:4]=1

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

生成物 1

HCID 579504804-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one収率 91%

反応条件

温度
80 °C

実験手順

4-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide (600 mg, 2.22 mmol) was heated to 140° C. in acetic anhydride (20 mL) for 2 h. The mixture was concentrated and then heated at 80° C. for 1 h in a mixture of MeOH (10 mL) and aqueous 1 N NaOH (10 mL). The resultant black solution was concentrated to a volume of 10 mL and extracted with CHCl3/EtOH (3:1). The organic layer was removed and concentrated to provide the title compound (550 mg, 91%) as a tan solid: 1H NMR (300 MHz, CD3OD) δ 7.70-7.60 (m, 4H), 7.41 (d, J=7.0 Hz, 1H), 6.17 (dd, J=7.0, 2.5 Hz, 1H), 5.96 (d, J=2.4 Hz, 1H), 5.18 (s, 2H).

後処理

  1. concentrationThe mixture was concentrated
  2. concentrationThe resultant black solution was concentrated to a volume of 10 mL
  3. extractionextracted with CHCl3/EtOH (3:1)
  4. customThe organic layer was removed
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c740a6f9da54177bb895d4fbbff3e89
出典データセット
uspto-grants-2016_03
特許番号
US09296743B2

反応ノート

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