Ammonium Carbonate → 5-Amino-3-chloro-5,6,7,8-tetrahydro-5-quinolinecarboxylic acid

HRID 1591255ノート

反応式

HRID 1591255 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3([C:16]=2[CH:17]=1)[C:13](=[O:14])NC(=O)[NH:10]3.[OH-].[Ba+2].[OH-].C(=O)([O-])[O-:22].[NH4+].[NH4+]>O>[NH2:10][C:9]1([C:13]([OH:14])=[O:22])[CH2:8][CH2:7][CH2:6][C:5]2[N:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:16]1=2

参加物

5

反応物 3

HCID 517111Ammonium CarbonateHCID 6093286Barium hydroxideHCID 109995133-Chlorospiro-[5,6,7,8-tetrahydroquinolin-5,4'-imidazolidine]-2',5'-dione

生成物 1

HCID 108788835-Amino-3-chloro-5,6,7,8-tetrahydro-5-quinolinecarboxylic acid収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

3-Chlorospiro-[5,6,7,8-tetrahydroquinolin-5,4'-imidazolidine]-2',5'-dione, (20 grams, 0.0795 mol) and barium hydroxide (50 grams, 0.159 mol) in water (300 ml) were heated at reflux for 48 hours. The solution was cooled to 50° C. and ammonium carbonate (16 grams, 0.167 mol) was added in portions. After 0.5 hours, the aqueous suspension was filtered and the solids washed with warm water. The filtrate was evaporated in vacuo to a solid. This was slurried in isopropanol (200 ml) was the solvent was again evaporated. The residual solid was suspended in isopropanol (125 ml) and ether (125 ml), granulated for 1 hour, and collected by filtration. The amino acid was dried in vacuo; 13.68 grams, 75% yield. mp 213°-14.5° C. (dec.) NMR (DMSO-d6, 300 MHz) δ8.46 (d, 1), 7.88 (d, 1), 3.5 (br s, NH3), 2.80 (t, 2), 2.27 (m, 1), 2.10 (m, 1), 1.88 (m, 2).

後処理

  1. temperatureat reflux for 48 hours
  2. filtrationthe aqueous suspension was filtered
  3. washthe solids washed with warm water
  4. customThe filtrate was evaporated in vacuo to a solid
  5. customwas again evaporated
  6. waitether (125 ml), granulated for 1 hour
  7. filtrationcollected by filtration
  8. dry with materialThe amino acid was dried in vacuo

出典と根拠

ORDレコード
ord-c698e60ee47b4188aeb7a28ce753eb39
出典データセット
uspto-grants-1993_04
特許番号
US05206367

反応ノート

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