Hydrochloric Acid → 7-Chloro-2-methyl-[1,6]naphthyridin-3-ol

HRID 715095Notes

Reaction equation

HRID 715095 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH:9]=O.[OH-].[K+].O.Cl.[CH2:15]1C[O:18][CH2:17][CH2:16]1>>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[C:17]([OH:18])[C:16]([CH3:15])=[N:1]2)=[CH:4][N:5]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 454801984-Amino-6-chloropyridine-3-carbaldehyde

Product 1

HCID 898156237-Chloro-2-methyl-[1,6]naphthyridin-3-olYield 93%

Procedure

Treat a mixture of 4-amino-6-chloro-pyridine-3-carbaldehyde (39 g, 0.25 mol) and 2-hydroxy acetone (28 g, 0.375 mol) in THF (400 mL) with KOH (52.5 g, 0.75 mol), stir at RT for 1 h, add water and acidify with 1N HCl. Collect the resulting solids by filtration, wash with water (3×), then EtOAc (2×) and dry to afford the title compound (45 g, 93%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 7.77 (s, 1H), 7.53 (s, 1H), 2.54 (s, 3H).

Workup

  1. additionTreat
  2. customCollect the resulting solids
  3. filtrationby filtration
  4. washwash with water (3×)
  5. dry with materialEtOAc (2×) and dry

Sources & evidence

ORD record
ord-b6e4c4800a5649ac966edd25f92558af
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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