Ethyl 3-pyridylacetate → HCID 58133377, compound

HRID 878386Notes

Reaction equation

HRID 878386 reaction equation
CO[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[NH2:10].[O-]CC.[Na+].C([O:18][C:19](=O)[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)C>CN(C)C=O>[OH:11][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:19](=[O:18])[C:20]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 96490Ethyl 3-pyridylacetateHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 58133377HCID 58133377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-amino-nicotinic acid methyl ester (200 mg) (Example 1.1) in N,N-dimethylformamide (“DMF”) (2 ml) was added sodium ethoxide (21 μl) (21% by weight in ethanol) followed by ethyl-3-pyridyl-acetate (200 μl). The reaction mixture was heated in the microwave at 150° C. for 15 minutes. The mixture was quenched by addition of aqueous hydrochloric acid (2M) (0.72 ml) and then diluted with water. The precipitate was isolated by filtration and washed with water and finally triturated with diethyl ether to give 4-hydroxy-3-pyridin-3-yl-1H-[1,8]naphthyridin-2-one as a beige solid (109 mg). 1H-NMR (400 MHz, d6-DMSO): 11.75 (bs, 1H), 8.70 (m, 1H), 8.52-8.53 (dd, 1H), 8.48-8.49 (dd, 1H), 8.35-8.37 (dd, 1H), 7.98 (d, 1H), 7.45-7.49 (dd, 1H), 7.23-7.26 (dd, 1H) ppm.

Workup

  1. customThe mixture was quenched by addition of aqueous hydrochloric acid (2M) (0.72 ml)
  2. additiondiluted with water
  3. customThe precipitate was isolated by filtration
  4. washwashed with water
  5. customfinally triturated with diethyl ether

Sources & evidence

ORD record
ord-282b2b440cb64dae8c12a730142ece6b
Source dataset
uspto-grants-2015_03
Patent number
US08987455B2

Reaction notes

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