Sodium Iodide → 4-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-7-(2-morpholin-4-yl-ethoxy)-quinoline-3-carbonitrile

HRID 612040Notes

Reaction equation

HRID 612040 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([OH:25])[CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:26][CH3:27].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[I-].[Na+]>COCCOC>[OH:25][C:20]1[CH:19]=[C:18]([NH:17][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[C:6]([O:26][CH3:27])[CH:7]=3)[N:12]=[CH:11][C:10]=2[C:15]#[N:16])[CH:23]=[CH:22][C:21]=1[CH3:24]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 224666497-(2-Chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

Product 1

HCID 224665404-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-7-(2-morpholin-4-yl-ethoxy)-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1 g (2.38 mmol) of 7-(2-chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile, 3.4 g (39 mmol) of morpholine, and 0.08 g of sodium iodide in 22 ml ethylene glycol dimethyl ether refluxed for 34 hr. The solvent was removed and the residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated and dried over magnesium sulfate. Solvent was removed and the residue was chromatographed on silica gel eluting with ethyl acetate-methanol-triethylamine 70:30:2.5 giving 1.05 of the title compound as a light orange solid: mass spectrum (electrospray, m/e) M+H 435.0; (M+2H)+2 218.0.

Workup

  1. temperaturerefluxed for 34 hr
  2. customThe solvent was removed
  3. additionthe residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed
  7. customthe residue was chromatographed on silica gel eluting with ethyl acetate-methanol-triethylamine 70:30:2.5 giving 1.05 of the title compound as a light orange solid

Sources & evidence

ORD record
ord-78dcb500ee5b40a19245edce90243971
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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