Hydrochloric Acid → 9-Bromo-5-cyanomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52565ノート

反応式

HRID 52565 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17]I)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[C-:19]#[N:20].[Na+].O.Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:19]#[N:20])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8929Sodium CyanideHCID 544452219-Bromo-5-iodomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

生成物 1

HCID 538255809-Bromo-5-cyanomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione収率 24.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

A mixture of 9-bromo-5-iodomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (Example 36) (632 mg, 1.5 mmol) and sodium cyanide (147 mg, 3 mmol) in DMF (5 mL) was heated at 40° C. for 14.5 h. The mixture was poured into water, acidified by addition of 1N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with ethyl acetate to 1% acetic acid/ethyl acetate to give 117 mg of the title compound (24%): mp>280° C.; 1H NMR (270 MHz, DMSO-d6) δ12.10 (bs, 1H), 7.23 (s, 1H), 7.16 (s, 1H), 4.97~5.07 (m, 1H), 2.74~3.10 (m, 4H), 2.20 (dm, 1H, J=13.5 Hz), 1.87~2.03 (m, 1H).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with ethyl acetate to 1% acetic acid/ethyl acetate

出典と根拠

ORDレコード
ord-2f20a6ddb9c24667bf8f29f9909b4a15
出典データセット
uspto-grants-1997_04
特許番号
US05616586

反応ノート

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