Water → HCID 19913835, compound

HRID 1110910Notes

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[CH:37]=[CH:36][C:25]2[C:26](=[O:35])[CH:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:29][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:30]([C:28]1[O:29][C:24]2[CH:23]=[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:37]=[CH:36][C:25]=2[C:26](=[O:35])[CH:27]=1)([O:32][CH2:33][CH3:34])=[O:31]

Participants

Conditions

Temperature: 70 °C

Procedure

0.8 g of 2-(4-hydroxyphenoxy)methylquinoline, 0.99 g of 7-bromomethyl-2-carboethoxy-4-oxo-4H-1-benzopyran and 0.44 g of potassium carbonate are combined in 15 ml of dimethylformamide and heated at 70° C. for 18 hours. The mixture is poured into water and the aqueous mixture extracted with ethyl acetate. The organic solution is dried and evaporated and the resulting crude product is purified by column chromatography on silica gel to give 0.9 g of 2-carboethoxy-7-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran.

Workup

extractionthe aqueous mixture extracted with ethyl acetate
customThe organic solution is dried
customevaporated
customthe resulting crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-604ed3306d55474184e7d5e9a75e5a42
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04977162

Reaction notes

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