Sulfuric Acid → 7-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

HRID 925231ノート

反応式

HRID 925231 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14](N)[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH:18]S(O)(=O)=O.N([O-])=O.[Na+].C1COCC1>O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 23668193Sodium NitriteHCID 584948787-Amino-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

生成物 1

HCID 584953637-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester収率 66.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
70 °C

実験手順

Into a 250 ml flask, the product from step (b) (3 g, 12.82 mmol) dissolved in water (15 ml) and concentrated H2SO4 (1.02 ml, 19.23 mmol) was added The reaction mixture was heated to 70° C. and stirred for 15 minutes. A solution of NaNO2 (1.01 g, 14.74 mmol) in water (30 ml) was quickly added, followed by addition of THF (45 ml). The reaction mixture was stirred at 70° C. for 30 minutes and then allowed to cool to room temperature. The reaction mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the sub-title compound as a yellow solid (2.0 g) that was used without further purification. MS: ESI (positive): 236 (M+H).

後処理

  1. stirringThe reaction mixture was stirred at 70° C. for 30 minutes
  2. temperatureto cool to room temperature
  3. extractionThe reaction mixture was extracted with EtOAc (3×)
  4. washThe combined EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4, and solvent
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-c25dd445368a43d193e3442023421bb5
出典データセット
uspto-grants-2016_03
特許番号
US09284277B2

反応ノート

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