Water → HCID 13934583, compound

HRID 2118727Notes

Reaction equation

HRID 2118727 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][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:4](=[O:19])[C:3]=1[CH2:20][CH2:21]O.O.C([O-])(O)=O.[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2](=[O:1])[C:3]3[CH2:20][CH2:21][O:19][C:4]2=3)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 54717825HCID 54717825, compound

Product 1

HCID 13934583HCID 13934583, compound

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-hydroxy-3-(2-hydroxyethyl)-1-(4-methylphenyl)-1,8-naphthyridin-2(1H)-one (2.2 g.) in Eaton's Reagent (10% P2O5 in methane sulfonic acid; 40 ml.) was stirred in an atmosphere of nitrogen and 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 was recrystallized from isopropanol with decolorization to yield the product, m.p. 246°-248.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. washwashed with water, air
  4. customdried
  5. customwas recrystallized from isopropanol with decolorization
  6. customto yield the product, m.p. 246°-248.5° C.

Sources & evidence

ORD record
ord-8e967f86160247f68f569aafee94fd69
Source dataset
uspto-grants-1987_07
Patent number
US04680298

Reaction notes

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