Methane → HCID 178524728, compound

HRID 404585Notes

Reaction equation

HRID 404585 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=[O:13].[OH-].[Na+].C>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 178469618HCID 178469618, compound

Product 1

HCID 178524728HCID 178524728, compoundYield 62.2%

Procedure

Ethyl 4-hydroxy-1,6-naphthyridine-3-carboxylate (2.6 g, 11 mmol) was refluxed for six hours with sodium hydroxide (25 mL, 4%). The hot solution was decolorized with charcoal, filtered and acidified to pH 3. After cooling, the precipitate was removed by filtration, washed with water and dried to give the title compound (1.3 g) as a tan powder. 1H NMR (DMSO_d6): δ: 14.66 (s, 1H), 12.8-14 (br, 1H), 9.42 (s, 1H), 8.98 (s, 1H), 8.80 (d, J=5.6, 1H), 7.69 (d, J=5.6, 1H), MS (ESI) m/e (M+H+) 191.12.

Workup

  1. filtrationfiltered
  2. temperatureAfter cooling
  3. customthe precipitate was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9949e7fd9ddc4b64b77470e27b052edd
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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