Sodium Hydroxide → 1-Acetyl-8-nitro-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

HRID 1687568ノート

反応式

HRID 1687568 の反応式
[C:1]([N:4]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8][CH2:7][C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2].[OH-].[Na+].[N+:19]([O-])([OH:21])=[O:20].OS(O)(=O)=O>>[C:1]([N:4]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8][CH2:7][C:6]2[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 14798Sodium HydroxideHCID 672641101-Acetyl-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-oneHCID 71777668Sulfuric acid, mixt. with nitric acid

生成物 1

HCID 672645601-Acetyl-8-nitro-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one

反応条件

温度
0 °C

実験手順

1-Acetyl-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one (1.05 g, 4.82 mmol) was added to a 1/1 mixture of HNO3/H2SO4 (20 ml) at 0° C. The resulting solution was stirred at 0° C. for 3 h and allowed to warm to rt over 16 h. The reaction mixture was poured onto ice and neutralized with NaOH. The resulting ppt was filtered and washed with H2O to afford title compound as a pale orange solid. (600 mg, 47%). mp 253-256° C.; LCMS: m/z=264.25 (M+H+), HPLC (95% purity); 1H NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.24 (d, J=8.8 Hz, 1H), 7.79 (m, 1H), 7.69 (d, J=8.6 Hz, 1H). 4.65 (m, 1H), 4.38 (m, 1H), 4.11 (m, 1H), 2.96 (m, 1H), 2.61 (m, 1H), 2.38 (m, 1H), 1.73 (s, 3H).

後処理

  1. temperatureto warm to rt over 16 h
  2. filtrationThe resulting ppt was filtered
  3. washwashed with H2O

出典と根拠

ORDレコード
ord-e903579484004964967cb8ee4bf3640f
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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