Sodium Bicarbonate → 7-Amino-4-(2,4-dichloroanilino)-6-hydroxy-3-quinolinecarbonitrile

HRID 396190Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[CH:10][C:9]([O:22]C)=[C:8]([NH:24]C(=O)C)[CH:7]=2)#[N:2].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:24][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])=[C:3]([C:1]#[N:2])[CH:4]=[N:5]2)=[CH:10][C:9]=1[OH:22]

Participants

Conditions

Temperature: 200 °C

Procedure

An amount of 200 mg (0.50 mmol) of N-[3-cyano-4-(2,4-dichloroanilino)-6-methoxy-7-quinolinyl]acetamide, was stirred with pyridine hydrochloride (1.4 g, 12.5 mmol), and heated at 200° C. for 2 hours. The mixture was cooled to room temperature, stilled with ethyl acetate and saturated sodium bicarbonate solution, and filtered. The layers were separated, and the organic layer was subsequently washed with saturated brine solution, dried over sodium sulfate, and evaporated to a yellow oil. Purification was carried out by preparative thin layer chromatography (5% methanol in ethyl acetate), to yield a yellow solid (52 mg, 30% yield), mp 265° C. decomp.; 1H NMR (DMSO-d6) δ 10.26 (bs, 1H), 8.93 (s, 1H), 8.34 (s, 1H), 7.66 (d, J=2 Hz, 1H), 7.35 (dd, J=9Hz, J=2Hz, 1H), 7.32 (s, 1H), 7.10 (d, J=9 Hz, 1H), 6.99 (s, 1H), 5.90 (s, 2H); HRMS (EI) m/z 344.0897 (M+1). Analysis for C16H10Cl2N4O.0.5CH3OH: Found: C, 54.43; H, 3.12; N, 15.34. Calcd: C, 54.74; H, 3.32; N, 15.48.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered
customThe layers were separated
washthe organic layer was subsequently washed with saturated brine solution
dry with materialdried over sodium sulfate
customevaporated to a yellow oil
customPurification

Sources & evidence

ORD record: ord-b096b0b93d24485d8c8e58688429844b
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608048B2

Reaction notes

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