Trifluoroacetic anhydride → 1,3-Diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

HRID 1686973ノート

反応式

HRID 1686973 の反応式
[CH2:1]([CH:3]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH2:16][CH3:17])[C:4]1=[O:18])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:32]([O-])([O-:34])=[O:33].[K+].[OH-].[Na+]>CC#N.O>[CH2:1]([CH:3]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[C:12]([N+:32]([O-:34])=[O:33])=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH2:16][CH3:17])[C:4]1=[O:18])[CH3:2]

参加物

7

反応物 4

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 672637981,3-Diethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

生成物 1

HCID 672642751,3-Diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one収率 31%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

1,3-Diethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (564 mg, 2.28 mmol) was dissolved in 1 ml of anhydrous MeCN. The reaction was cooled to 0° C. and trifluoroacetic anhydride (3.00 mL, 21.2 mmol) and Potassium nitrate (230 mg, 2.28 mmol) were charged. The reaction was stirred for 1.5 h and then the reaction was basified with 1-2 ml of 30% NaOH solution and allowed to stir for 1 h. Pour reaction into 75 ml water and extract with 3×30 ml portions of methylene chloride. Dry the combined organic over magnesium sulfate and evaporate. Product is a yellow brown oil (625 mg). Crude material was chromatographed on a 40 g Isco column using 30-50% EtOAc in hexanes as the eluent to yield 1,3-diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (205 mg, 31%) as a tan waxy solid as a mixture of diastereomers.

後処理

  1. stirringto stir for 1 h
  2. additionPour
  3. extractionextract with 3×30 ml portions of methylene chloride
  4. dry with materialDry the combined organic over magnesium sulfate
  5. customevaporate
  6. customCrude material was chromatographed on a 40 g Isco column

出典と根拠

ORDレコード
ord-8e8d5cd2b5e641069f12aad17f1df54f
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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