Piperidine → 5,7-diethyl-3-methyl-1,6-naphthyridin-2(1H)-one

HRID 487395Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=O.N1CCCCC1.[CH3:20][CH:21](C(OCC)=O)[C:22](OCC)=[O:23]>>[CH2:10]([C:4]1[N:5]=[C:6]([CH2:8][CH3:9])[CH:7]=[C:2]2[C:3]=1[CH:12]=[C:21]([CH3:20])[C:22](=[O:23])[NH:1]2)[CH3:11]

Participants

Reactant 3

HCID 8082Piperidine

HCID 11857Diethyl methylmalonate

HCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

Product 1

HCID 190937345,7-diethyl-3-methyl-1,6-naphthyridin-2(1H)-one

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-amino-2,6-diethylpyridine-3-carbaldehyde (2.0 g), piperidine (0.5 ml) and diethyl methylmalonate (3.0 ml) was heated together at 120° C. for 24 hours. The mixture was then purified by flash chromatography, eluting with ether, to give 5,7-diethyl-3-methyl-1,6-naphthyridin-2(1H)-one as a solid (0.265 g); m.p. 163°-166° C. dec. (after recrystallisation from acetone); NMR (d6 -DMSO): 1.22(t, 3H), 1.24(t, 3H), 2.11(s, 3H), 2.71(q, 2H), 2.99(q, 2H), 6.88(s, 1H), 7.96(s, 1H), 11.84(broad, 1H); mass spectrum (CI, ammonia): 217 (M+H)+ ; microanalysis, found: C, 72.3; H, 7.4; N, 13.1%; C13H16N2O requires: C, 72.2; H, 7.5; N, 13.0%.

Workup

customThe mixture was then purified by flash chromatography
washeluting with ether

Sources & evidence

ORD record: ord-c8fe96a1998f4e69805ea1a0455d650e
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294620

Reaction notes

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