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

HRID 1591255Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-c698e60ee47b4188aeb7a28ce753eb39
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05206367

Reaction notes

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