Sodium Hydroxide → 4-Hydroxy-1-phenyl-3-(prop-2-en-1-yl)-1,8-naphthyridin-2(1H)-one

HRID 2412419Notes

Reaction equation

HRID 2412419 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7](=[O:21])[C:6]=1[CH2:22][CH:23]=[CH2:24])(=O)C.[OH-].[Na+]>C(O)C>[OH:4][C:5]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7](=[O:21])[C:6]=1[CH2:22][CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1459852-Oxo-1-phenyl-3-(prop-2-en-1-yl)-1,2-dihydro-1,8-naphthyridin-4-yl acetate

Product 1

HCID 546860954-Hydroxy-1-phenyl-3-(prop-2-en-1-yl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.0 g. of 4-acetoxy-1-phenyl-3-(2-propenyl)-1,8-naphthyridin-2(1H)-one, 200 ml. of ethanol and 40 ml. of 1N sodium hydroxide solution is stirred at room temperature for 22 hours. The ethanol is removed in vacuo and the remaining aqueous solution acidified with 1N hydrochloric acid. The product is filtered, washed with water and dried, weight 5.3 g., m.p. 248°-250° C. Recrystallization from chloroform yields the product of this example as a colorless solid, m.p. 250°-252° C.

Workup

  1. additionA mixture of 6.0 g
  2. customThe ethanol is removed in vacuo
  3. filtrationThe product is filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from chloroform
  7. customyields the product of this example as a colorless solid, m.p. 250°-252° C.

Sources & evidence

ORD record
ord-4fd262f23127424d9dafe1a2639ec222
Source dataset
uspto-grants-1985_01
Patent number
US04492702

Reaction notes

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