Sulfuric Acid → 1,8-Naphthyridin-2(1H)-one

HRID 903871Notes

Reaction equation

HRID 903871 reaction equation
N[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N([O-])=[O:13].[Na+].FC(F)(F)C(O)=O.S(=O)(=O)(O)O.[OH-].[NH4+]>O>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=[CH:11][C:2]1=[O:13]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 41730482-Amino-1,8-naphthyridineHCID 23668193Sodium Nitrite2×

Product 1

HCID 2996431,8-Naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 2-amino-1,8-naphthyridine (III) thus produced is converted to the diazonium salt with sodium nitrite in an acid, preferably trifluoroacetic acid or sulfuric acid. The diazonium salt is prepared at -5° C. or less during the addition, over a period of about 2 hours, of the sodium nitrite. The reaction mixture then is generally maintained at this temperature for an additional hour, and combined with a mixture of ice and water. The aqueous mixture is then made alkaline preferably with ammonium hydroxide, and the product 1,8-naphthyridine-2-(1H)-one (IV) isolated using known techniques.

Workup

  1. temperatureThe reaction mixture then is generally maintained at this temperature for an additional hour

Sources & evidence

ORD record
ord-ec437b369ead43aa9fced826a5c0ecbf
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

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