Acetic Acid → 6,7-Dimethoxy-4-[(1-oxo-2,3-dihydro-1H-inden-4-yl)amino]-3-quinolinecarboxamide

HRID 1822853

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17].[NH2:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][C:24]2=[O:29].C(O)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]([NH2:18])=[O:17])=[C:2]2[NH:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][C:24]2=[O:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.046 g, 0.17 mmol), 4-amino-1-indanone (0.036 g, 0.24 mmol) and acetic acid (40 μl) in DMF (0.6 ml) was heated at 100° C. for 1 h 45 min. After cooling, the mixture was diluted with water and made alkaline with saturated NaHCO3. The precipitate was collected by filtration, washed with water and dried to give title compound (59 mg, 90%).

Workup

temperatureAfter cooling
filtrationThe precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-a08ab8a4132a4a96847310ecd47f69b4
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037925B2

Linked notes

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