Potassium Carbonate → 2-cyano-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran

HRID 1090787Notes

Reaction equation

HRID 1090787 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[C:31]2[O:30][C:29]([C:32]#[N:33])=[CH:28][C:27](=[O:34])[C:26]=2[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OC(=O)C)C>[C:32]([C:29]1[O:30][C:31]2[C:22]([CH2:21][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)=[CH:18][CH:19]=3)=[CH:23][CH:24]=[CH:25][C:26]=2[C:27](=[O:34])[CH:28]=1)#[N:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109887374-[(Quinolin-2-yl)methoxy]phenolHCID 19913881HCID 19913881, compound

Product 1

HCID 199138832-cyano-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyranYield 27.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g of 2-(4-hydroxyphenoxy)methylquinoline, 1.0 g of 8-bromomethyl-2-cyano-4-oxo-4H-1-benzopyran and 0.5 g of potassium carbonate are stirred at room temperature in 5 ml of dimethylformamide for 2 days. The reaction mixture is diluted with ethylacetate, filtered and concentrated. The residue is chromatographed on silica gel to give 0.45 g of 2-cyano-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-81cdbee9a03f4da4919769b99e616f21
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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