Ethyl Acetate → HCID 22416898, compound

HRID 1721179Notes

Reaction equation

HRID 1721179 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[N:11]2)=[CH:6][CH:5]=1.[H-].[Na+].N[C:28]1C=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1.Cl[CH2:36][C:37]1C=CC2C(=CC(OC(F)(F)F)=CC=2)N=1.[C:52]([O:55]CC)(=[O:54])C>CN(C=O)C>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:17]=[C:18]([NH:19][C:30](=[O:34])[CH2:31][C:32]([CH2:33][CH3:28])([CH2:36][CH3:37])[C:52]([OH:55])=[O:54])[CH:20]=[CH:21][CH:22]=3)=[N:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 24758Sodium hydrideHCID 22416918HCID 22416918, compoundHCID 22416939HCID 22416939, compound

Product 1

HCID 22416898HCID 22416898, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(7-trifluoromethoxy-2-quinolinylmethoxy)aniline: 0.175 g of NaH (95%) is added at 0° to a solution of 0.754 g of 3-aminophenol in 20 ml of DMF and then the batch is stirred for 30 min. at 0°. 1.78 g of 2-chloromethyl-7-trifluoromethoxy-quinoline in solid form are then added and the batch is stirred for a further one hour at 0° and for another hour at 20°. It is then diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated by evaporation. The evaporation residue is chromatographed on 100 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 98:2 and 95:5 are combined and concentrated by evaporation to give the title compound which is further purified by crystallisation from CH2Cl2 /ether/hexane.

Workup

  1. stirringthe batch is stirred for a further one hour at 0° and for another hour at 20°
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by evaporation
  5. customThe evaporation residue is chromatographed on 100 g of silica gel
  6. washThe product-containing fractions eluted with toluene/ethyl acetate 98:2 and 95:5
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2f0ffba44b334f68bb5435eb7175373d
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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