Acetic Acid → HCID 178476732, compound

HRID 869450Notes

Reaction equation

HRID 869450 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[N+:6]([O-])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:12]([OH:15])(=[O:14])[CH3:13]>N1C=CC=CC=1.[Fe]>[C:12]([OH:15])(=[O:14])[CH3:13].[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:14])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3392321-Oxo-1lambda~5~-1,5-naphthyridine

Product 1

HCID 178476732HCID 178476732, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 1,5-naphthyridin-5-oxide 4-01 (D-5) (330 mg, 2.0 mmol, 1.0 eq) in acetic acid (12 mL) and pyridine (2.5 mL) at RT, iron powder (456 mg, 8.15 mmol, 4.0 eq) is added in portions (over 10 min) and the resulting mixture is stirred for 2 h. The mixture is filtered and the solid is rinsed with acetic acid. The filtrate is concentrated in vacuo. The residue is triturated with acetone and then filtered. The filter cake is rinsed with acetone and dried in vacuo to afford the product, 1,5-naphthyridin-4-ol acetic acid salt (D-6).

Workup

  1. filtrationThe mixture is filtered
  2. washthe solid is rinsed with acetic acid
  3. concentrationThe filtrate is concentrated in vacuo
  4. customThe residue is triturated with acetone
  5. filtrationfiltered
  6. washThe filter cake is rinsed with acetone
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d92b4189a0ae44c4877aabd49bd8f0f2
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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