Ammonium Hydroxide → Pyrano[2,3-f]quinolin-4-one

HRID 47059Notes

Reaction equation

HRID 47059 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+]>>[O:11]1[C:6]2=[C:5]3[C:10](=[CH:9][CH:8]=[C:7]2[C:14](=[O:16])[CH:13]=[CH:12]1)[N:1]=[CH:2][CH:3]=[CH:4]3

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 203850343-(5-Quinolinoxy)-propionic acid

Product 1

HCID 20385029Pyrano[2,3-f]quinolin-4-one

Procedure

Polyphosphoric acid (26 ml) was heated at 90°-95° C. and stirred while 3-(5-quinolinoxy)-propionic acid (2.60 g, 0.0120 mole) was added in small portions. After heating for 2 hours the mixture was poured into 200 ml ice water, basified to pH 10 with concentrated ammonium hydroxide and extracted with 3×200 ml ethyl acetate. The combined organic plasma were dried over magnesium sulfate, filtered, and evaporated in vacuo to a solid, which were recrystallized from toluene, m.p. 146°-147° C.

Workup

  1. additionwas added in small portions
  2. temperatureAfter heating for 2 hours the mixture
  3. extractionextracted with 3×200 ml ethyl acetate
  4. dry with materialThe combined organic plasma were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a solid, which
  7. customwere recrystallized from toluene, m.p. 146°-147° C.

Sources & evidence

ORD record
ord-4f38e8e82f3648c792a79f6649eba931
Source dataset
uspto-grants-1979_11
Patent number
US04176185

Reaction notes

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