Potassium Hydroxide → 2-(2-Thiazolyl)-1,8-naphthyridine

HRID 831

Reaction equation

HRID 831 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)(=O)[CH3:11].[OH-].[K+]>CO>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[C:10]1[CH:11]=[CH:4][C:3]2[C:2](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5201082-AcetylthiazoleHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 157902072-(2-Thiazolyl)-1,8-naphthyridineYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Aminonicotinaldehyde (1.5 g, 12.3 mmol) and 2-acetylthiazole (1.64 g, 12.9 mmol) are dissolved in 12 ml of MeOH and the mixture is treated with 1.5 ml of 40% KOH. After 3 h, the reaction is complete and the mixture is poured onto water. The solid which is deposited is filtered off with suction, washed and dried. 1.22 g (yield 46%) of the desired product are obtained. M.p. 160°-165° C.

Workup

  1. additionthe mixture is poured onto water
  2. filtrationThe solid which is deposited is filtered off with suction
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-6da8fccbc46d48d9b47085df7224e0c2
Source dataset
uspto-grants-1998_03
Patent number
US05723413

Linked notes

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