Tetrahydrofuran → 6-amino-4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone

HRID 2209975Notes

Reaction equation

O1CCCC1.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-])=O)[CH:31]=4)[NH:26][C:25](=[O:36])[CH:24]=3)[CH2:17][CH2:16]2)=[CH:7]1>CO>[NH2:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:36])[CH:24]=[C:23]2[CH2:22][CH2:21][N:18]1[CH2:17][CH2:16][CH:15]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:6][CH:7]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 55 °C

Procedure

Into a mixed solvent of tetrahydrofuran (800 ml) and methanol (200 ml) was dissolved 4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-6-nitro-2(1H)-quinolinone (III-19) (6 g, 14.4 mmol) under heating. Paladium on carbon (2.5 g) was added thereto and the mixture was stirred under hydrogen atmosphere at 55 ° C. for 4 hours. The reaction mixture was filtered at the same temperature and the solvent was distilled off from the filtrate. The residue was dried and then recrystallized from a mixture of methanol, THF and water to give the desired product (III-20) (4.3 g) as pale yellow crystals (mp 214°-216 ° C. (methanol/tetrahydrofuran water)). Yield 77.3 %.

Workup

temperatureunder heating
additionPaladium on carbon (2.5 g) was added
filtrationThe reaction mixture was filtered at the same temperature
distillationthe solvent was distilled off from the filtrate
customThe residue was dried
customrecrystallized from a mixture of methanol, THF and water

Sources & evidence

ORD record: ord-ac9aff5d334c4a528ded1df787b81043
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457099

Reaction notes

Loading…