Ethyl Acetate → HCID 178516441, compound

HRID 525369Notes

Reaction equation

HRID 525369 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[F:26][C:27]1[CH:28]=[C:29]([NH:33][CH:34]=[C:35]2[C:40](=[O:41])OC(C)(C)OC2=O)[CH:30]=[N:31][CH:32]=1.CCOC(C)=O>C(OCC)C>[F:26][C:27]1[CH:28]=[C:29]2[C:30]([C:40]([OH:41])=[CH:35][CH:34]=[N:33]2)=[N:31][CH:32]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 675034075-((5-Fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178516441HCID 178516441, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of Dowtherm A at 250° C., was added 5-(((5-fluoropyridin-3-yl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1 g, 0.003 mol) portionwise over a period of 10 minutes. The reaction was monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether, uv active). After completion of reaction, the mixture was cooled to ambient temperature and treated with diethyl ether to obtain a grey precipitate. The precipitate was stirred for 5-10 minutes and filtered, washed with diethyl ether and dried under vacuum to obtain 7-fluoro-1,5-naphthyridin-4-ol as a tan colored solid, (0.4 g, 64.93%). 1H NMR (400 MHz, DMSO-d6): δ 12.68 (bs, 1H), 9.43 (s, 1H), 8.75 (t, J=6.4 Hz, 1H), 8.59 (d, J=8, 1H), 6.99 (d, J=17.2 Hz, 1H). m/z (ESI) 165.1 (M+H)+.

Workup

  1. customAfter completion of reaction
  2. customto obtain a grey precipitate
  3. filtrationfiltered
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f0faf7c99d694e7783d7fcc6c66610ef
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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