Sodium Iodide → 6-(1-Aziridinyl)-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile

HRID 548498Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 0.202 g (0.5 mmol) of 6-[(2-chloroethyl) amino]-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile in 4 ml of dimethylformamide, were added 0.075 g of sodium iodide (0.5 mmol) and 0.069 g of potassium carbonate (0.5 mmol). After the reaction solution was heated at 75° C. overnight, it was decanted into cold saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. The solvent was removed to yield 0.19 g of a light brown solid. The crude product was washed with hexane to give 0.1 g of a yellow solid, mp 197-199° C.; high resolution mass spectrometry (EI, m/e): M 368.0888.

Workup

customit was decanted into cold saturated sodium bicarbonate solution
customThe organic layer was separated
dry with materialdried over sodium sulfate
customThe solvent was removed

Sources & evidence

ORD record: ord-fb722fc4f5304ddf88eb410ee3aad603
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042376E1

Reaction notes

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