Acetic Acid → HCID 178516427, compound

HRID 1473502Notes

Reaction equation

HRID 1473502 reaction equation
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:13])=[CH:5][CH:6]=[N:7]2.C(O)(=O)C>[Zn].CO>[Cl:12][C:10]1[CH:9]=[C:8]2[C:3]([C:4]([OH:13])=[CH:5][CH:6]=[N:7]2)=[CH:2][N:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178516428HCID 178516428, compound

Product 1

HCID 178516427HCID 178516427, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5,7-dichloro-1,6-naphthyridin-4-ol (1.6 g, 7.44 mmol) was added to a round bottom flask, followed by zinc (2.432 g, 37.2 mmol) and MeOH (44.6 mL). Acetic acid (glacial) (4.26 mL, 74.4 mmol) was added and the reaction was heated to 60° C. for 16 hours. The solids were filtered and washed with MeOH (20 mL). The filtrate was concentrated under reduced pressure to provide 1.03 g of 7-chloro-1,6-naphthyridin-4-ol as a white solid which was used without further purification. m/z (ESI) 181.2 (M+H)+.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with MeOH (20 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c441068bb5a04a37b15aadc090771c46
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…