HCID 178471941, compound → Ethyl 4-hydroxy-3,4-dihydro-1,5-naphthyridine-3-carboxylate

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[N:7]=[CH:8]/[CH:9]([C:15]([O:17]CC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=1>O(C1C=CC=CC=1)C1C=CC=CC=1>[OH:17][CH:15]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][N:1]=2)[N:7]=[CH:8][CH:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 250 °C

Procedure

Diethyl [(E)-(pyridin-3-ylimino)methyl]malonate (9 g, 34 mmol) was dissolved in 1,1′-oxydibenzene (150 ml). The mixture was heated at 250° C. for 2 hours, and then cooled to room temperature. The reaction mixture was filtered to give ethyl 4-hydroxy-3,4-dihydro-1,5-naphthyridine-3-carboxylate.

Workup

temperaturecooled to room temperature
filtrationThe reaction mixture was filtered

Sources & evidence

ORD record: ord-c8cab84f26644dd2b6cbc67822f071e7
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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Participants

Reactant 1

HCID 178471941HCID 178471941, compound

Product 1

HCID 67207071Ethyl 4-hydroxy-3,4-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent