1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → 1-(4-Hydroxy-6-methoxy-1,5-naphthyridin-3-yl)ethanone

HRID 2178875Notes

Reaction equation

HRID 2178875 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31]([NH:34][CH:35]=[C:36]([C:42](=[O:44])[CH3:43])[C:37]([O:39]CC)=O)=[CH:30][CH:29]=1>>[OH:39][C:37]1[C:32]2[C:31](=[CH:30][CH:29]=[C:28]([O:27][CH3:26])[N:33]=2)[N:34]=[CH:35][C:36]=1[C:42](=[O:44])[CH3:43]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 178471946HCID 178471946, compound

Product 1

HCID 1784878671-(4-Hydroxy-6-methoxy-1,5-naphthyridin-3-yl)ethanoneYield 98.2%

Procedure

To a flask containing Dowtherm™ A (500 mL) at 250° C. was added ethyl 2-[(6-methoxypyridin-3-ylamino)methylene]-3-oxobutanoate (75 g, 0.28 mol) portion wise over 3 to 5 min and the reaction mixture was stirred for an additional 30 to 60 min. The reaction mixture was removed from the heat source, cooled to room temperature and diluted with hexanes to facilitate precipitation. The solids were filtered, washed with hexanes and acetonitrile and dried under vacuum to afford the desired product (60 g, 46%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 12.48 (bs, 1H), 8.45 (d, J=5.2 Hz, 1H), 8.00 (d, J=8.9 Hz, 1H), 7.40-7.37 (m, 1H), 7.21 (d, J=8.9 Hz, 1H), 7.01-6.99 (m, 1H), 3.96 (s, 3H), 2.61 (s, 3H); ESI MS m/z 219 [M+H]+.

Workup

  1. customThe reaction mixture was removed from the heat source
  2. additiondiluted with hexanes
  3. customprecipitation
  4. filtrationThe solids were filtered
  5. washwashed with hexanes and acetonitrile
  6. customdried under vacuum

Sources & evidence

ORD record
ord-154a8d78843f4d17832bc4a94fa3c20d
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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