Water → 3,9-Dihydro-9-phenyl-furo[2,3-b][1,8]-naphthyridin-4(2H)-one

HRID 1906416Notes

Reaction equation

HRID 1906416 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=O)[C:3]=1[CH2:19][CH2:20][OH:21].O.C([O-])(O)=O.[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[C:12]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2](=[O:1])[C:3]3[CH2:19][CH2:20][O:21][C:4]2=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 547236674-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 138234683,9-Dihydro-9-phenyl-furo[2,3-b][1,8]-naphthyridin-4(2H)-one

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one in Eaton's Reagent (10% P2O5 in methane sulfonic acid; 40 ml.) was stirred in an atmosphere of nitrogen and was heated to 70° C. for 2 hr. After cooling, the product was poured into water, adjusted to pH 4 with NaHCO3, filtered, washed with water, air dried and recrystallized from isopropanol with decolorization to yield the product, m.p. 245°-247° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. washwashed with water, air
  4. customdried
  5. customrecrystallized from isopropanol with decolorization
  6. customto yield the product, m.p. 245°-247° C.

Sources & evidence

ORD record
ord-d98d97b37cdd49e0b96bd6d1f3e82b91
Source dataset
uspto-grants-1987_03
Patent number
US04652564

Reaction notes

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