1,6-Naphthyridine → 1,6-naphthyridin-5(6H)-one

HRID 2354128Notes

Reaction equation

HRID 2354128 reaction equation
N1C2C(=CN=CC=2)C=CC=1.[N:11]1[C:20]2[CH:19]=[CH:18][NH:17][C:16](=[O:21])[C:15]=2[CH:14]=[CH:13][C:12]=1C=O>>[N:11]1[C:20]2[CH:19]=[CH:18][NH:17][C:16](=[O:21])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 674881,6-NaphthyridineHCID 87452630HCID 87452630, compound

Product 1

HCID 55203681,6-naphthyridin-5(6H)-one

Procedure

Reaction Scheme V illustrates the preparation of 1,6-naphthyridin-5(6H)-one compounds. In the initial condensation of N-Boc-protected 2-chloro-4-amino-nicotinaldehyde with the (substituted phenyl)benzyl ketone (V-1) in the presence of an alkoxide, such as, sodium methoxide, there is obtained directly the 1,6-naphthyridine (V-2) substituted at the 5-position with the alkoxide group. Acid catalyzed hydrolysis readily converts the 1,6-naphthyridine to the requisite 1,6-naphthyridin-5(6H)-one aldehyde functionality (V-3) and this material can undergo reductive amination with a diverse array of amines to give the 1,6-naphthyridin-5(6H)-one compounds (V-6).

Workup

  1. customhydrolysis

Sources & evidence

ORD record
ord-81d189d2cfd84208913a06dd42ec228a
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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