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

HRID 1591255노트

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HRID 1591255 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c698e60ee47b4188aeb7a28ce753eb39
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206367

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