HCID 15696724, compound → HCID 135666682, compound

HRID 638207Notes

Reaction equation

HRID 638207 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13](=[O:19])[NH:14]3)=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13](=[O:19])[NH:14]3)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 15696724HCID 15696724, compound

Product 1

HCID 135666682HCID 135666682, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture containing 12.6 g of 5-(4-methoxyphenyl)-1,6-naphthyridin-2(1H)-one and 100 ml of 40% aqueous hydrogen bromide was refluxed for 14 hours, cooled and evaporated on a rotary evaporator. The remaining solution was neutralized by adding aqueous ammonium hydroxide solution. The resulting yellow solid was collected, washed with water, dried, recrystallized from dimethylformamide and dried in a vacuum oven at 90°-95° C. to yield 11.2 g of 5-(4-hydroxyphenyl)-1,6-naphthyridin-2(1H)-one, m.p. >300° C.

Workup

  1. temperaturewas refluxed for 14 hours
  2. temperaturecooled
  3. customevaporated on a rotary evaporator
  4. additionby adding aqueous ammonium hydroxide solution
  5. customThe resulting yellow solid was collected
  6. washwashed with water
  7. customdried
  8. customrecrystallized from dimethylformamide
  9. customdried in a vacuum oven at 90°-95° C.

Sources & evidence

ORD record
ord-48fbb6145fd442229f72d6f353a97fb7
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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