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ChemicalBook CAS DataBase List 7-METHYL-3,4-DIHYDRO-2H-[1,8]NAPHTHYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

7-METHYL-3,4-DIHYDRO-2H-[1,8]NAPHTHYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

11synthesis methods
24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
821 suppliers
$13.50/25G

274676-47-0 Synthesis
1,8-Naphthyridine,1,2,3,4-tetrahydro-7-methyl-(9CI)

274676-47-0
37 suppliers
$69.40/250mg

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Yield:243641-37-4 90%

Reaction Conditions:

at 75; for 18 h;Neat (no solvent);

Steps:

9.D

Step DTo the title compound from Step C above (7.42 g, 50.13 mmol) was added a solution of di-tert-butyl dicarbonate (33.7 g, 150.4 mmol) in dichloromethane (100 mL). The solvent was removed and the oily residue was heated at 75° C. in a sand bath for 18 h. The reaction mixture was purified by chromatography on silica using ethyl acetate/n-heptane (10/90) to remove excess di-tert-butyl dicarbonate followed by ethyl acetate/n-heptane (40/60) to afford the title compound as a white solid (11.2 g, 90%).1H-NMR (400 MHz, CDCl3): δ=1.52 (s, 9H), 1.87-1.93 (m, 2H), 2.46 (s, 3H), 2.70 (t, 2H), 3.72 (t, 2H), 6.80 (d, 1H), 7.24 (d, 1H)

References:

US2011/92537,2011,A1 Location in patent:Page/Page column 44

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