Réaction #84059

Équation de réaction

2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline

→

Compound 2

Rendement 38.1%

2-(4-(1H-tetrazol-5-yl)phenyl)-3-methylquinolin-6-ol

Rendement 38.1%

Solvants

NMP

Conditions de réaction

Traitement

1. 1
   ConcentrationAfter concentration in vacuo the crude
2. 2
   workup.DISSOLUTIONwas dissolved in 5 mL of 1N NaOH
3. 3
   FiltrationThe solids were filtered
4. 4
   Autredried in vacuo

Mode opératoire

2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline (128 mg, 0.40 mmol) was dissolved in 5 mL of NMP and Na2S (47 mg, 0.60 mmol) was added to it. The mixture was then stirred for 4 hours at 140° C. in a microwave reactor. After concentration in vacuo the crude was dissolved in 5 mL of 1N NaOH and slowly acidified with 1N HCl to a pH of 4. The solids were filtered and dried in vacuo to afford 46.2 mg (38% yield) of Compound 2. 1H NMR (DMSO-d6, 400 MHz): δ 10.10-10.00 (bs, 1H), 8.18-8.15 (d, 2H), 8.08 (s, 1H), 7.87-7.84 (m, 3H), 7.30-7.26 (d, 1H), 7.13 (s, 1H), 2.45 (s, 3H). MS (ESI): m/z 304.11 [M+H]+.

Source