Sodium Carbonate → HCID 90143070, compound

HRID 2175748Notes

Reaction equation

HRID 2175748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]1([CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[CH2:5]2.C([O-])([O-])=O.[Na+].[Na+].Cl.[NH2:26][OH:27]>C(O)C.O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]1([CH2:17][CH2:16][C:15](=[N:26][OH:27])[CH2:14][CH2:13]1)[CH2:5]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 90143068HCID 90143068, compound

Product 1

HCID 90143070HCID 90143070, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 6′-bromo-1′H-spiro[cyclohexane-1,3′-[1,8]naphthyridine]-2′,4(4′H)-dione (P) (0.35 g, 1.13 mmol) in ethanol/water (18 mL/2 mL) were added Na2CO3 (0.6 g, 5.68 mmol) and hydroxylamine hydrochloride (0.39 g, 5.68 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 4 h. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get the desired compound as an off-white solid (200 mg, 95%); 1H NMR (400 MHz, DMSO-d6) δ 10.69 (s, 1H), 10.28 (s, 1H), 8.23 (d, J=2.4 Hz, 1H), 7.88 (d, J=2.0 Hz, 1H), 2.99 (s, 2H), 2.30-2.16 (m, 4H), 1.84-1.66 (m, 2H), 1.50-1.38 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe organic layer was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was rotary evaporated under vacuum

Sources & evidence

ORD record
ord-16dd9fb7d07345cc82fec6d336e77ac5
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

Loading…