Methanol → HCID 178510307, compound
Reaction equation
[C:1]([C:3](=[CH:9][NH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:4]([O:6]CC)=O)#[N:2].CO.C(Cl)Cl>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:6][C:4]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][N:13]=2)[N:10]=[CH:9][C:3]=1[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 260 °C
Procedure
The mixture of ethyl 2-cyano-3-(pyridin-3-ylamino)acrylate (C-3) (2.0 g, 9.26 mmol, 1.0 eq) in Dowtherm A (48 mL) is stirred at 260° C. for 5 h. The mixture is cooled to RT and poured into a mixture of MeOH and DCM (v/v=1:2, 20 mL). The precipitate is filtered, rinsed with DCM, and dried in vacuo to afford the product, 4-hydroxy-1,5-naphthyridine-3-carbonitrile (C-4).
Workup
- temperatureThe mixture is cooled to RT
- filtrationThe precipitate is filtered
- washrinsed with DCM
- customdried in vacuo
Sources & evidence
- ORD record
- ord-2dba3005c4af41d1a204f41f12afcc9d
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969363B2
Reaction notes
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