Ethyl Acetate → HCID 22416930, compound

HRID 1721184Notes

Reaction equation

HRID 1721184 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])[CH:6]=[CH:5]2.[H-].[Na+].N[C:25]1C=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.ClCC1C=CC2C(=C[C:38]([CH3:45])=C(C)C=2)N=1.[C:46]([O:49]CC)(=[O:48])C>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[C:7]([CH2:13][O:14][C:15]1[CH:16]=[C:17]([NH:18][C:27](=[O:31])[CH2:28][C:29]([CH2:30][CH3:25])([CH2:38][CH3:45])[C:46]([OH:49])=[O:48])[CH:19]=[CH:20][CH:21]=1)[CH:6]=[CH:5]2

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 24758Sodium hydrideHCID 22416869HCID 22416869, compoundHCID 22416899HCID 22416899, compound

Product 1

HCID 22416930HCID 22416930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(6,7-dimethyl-2-quinolinylmethoxy)aniline: 0.35 g of NaH (95%) is added at 0° to a solution of 1.51 g of 3-aminophenol in 30 ml of DMF and then the batch is stirred for 30 min. at 0°. 2.8 g of 2-chloromethyl-6,7-dimethyl-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 250 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 95:5 and 9:1 are combined and concentrated by evaporation to give the title compound which is further purified by crystallisation from CH2Cl2 /ether.

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 250 g of silica gel
  6. washThe product-containing fractions eluted with toluene/ethyl acetate 95:5 and 9:1
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d85fca0a683a4e8fa463119351a244b9
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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