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

HRID 1687568노트

반응식

HRID 1687568 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e903579484004964967cb8ee4bf3640f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

반응 노트

불러오는 중…