Water → HCID 13934589, compound

HRID 2118686Notes

Reaction equation

HRID 2118686 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:18])[C:3]=1[CH2:19][CH2:20][CH2:21]O.O.C([O-])(=O)C.[K+]>Br>[C:12]1([N:5]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]3[O:1][CH2:21][CH2:20][CH2:19][C:3]=3[C:4]2=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 547165494-Hydroxy-3-(3-hydroxypropyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 13934589HCID 13934589, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 4-hydroxy-3-(3-hydroxypropyl)1-phenyl-1,8-naphthyridin-2(1H)-one (5.67 g.) in 47% HBr (50 ml.) was stirred in an atmosphere of nitrogen and was heated to 90° C. for 5 hrs. After cooling, the product was poured into water, and the pH was adjusted to 4.5 with potassium acetate. Chromatographic purification of the product on silica gel eluting with CH2Cl2 : 5% ether and subsequent recrystallization of the product from the relevant fractions yielded the product, m.p. 253°-255° C.

Workup

  1. temperatureAfter cooling
  2. customChromatographic purification of the product on silica gel eluting with CH2Cl2
  3. custom5% ether and subsequent recrystallization of the product from the relevant fractions
  4. customyielded the product, m.p. 253°-255° C.

Sources & evidence

ORD record
ord-0106843b73ae418caa03c4497f451f80
Source dataset
uspto-grants-1987_07
Patent number
US04680297

Reaction notes

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