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

HRID 1248947Notes

Reaction equation

HRID 1248947 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-68577c7f14b84639b4beacbabf19fb7e
Source dataset
uspto-grants-1986_12
Patent number
US04628055

Reaction notes

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