Chloride → HCID 57815430, compound

HRID 509630Notes

Reaction equation

HRID 509630 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][CH:8]=[N+:9]([O-])[C:10]=2[CH:11]=1.[Cl-].C(=O)([O-])[O-:15].[K+].[K+]>C(Cl)(Cl)Cl.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 312ChlorideHCID 11430Potassium CarbonateHCID 57815209HCID 57815209, compound

Product 1

HCID 57815430HCID 57815430, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a mixture of 3-bromo-1,5-naphthyridine-5-oxide (C-3) (70.0 g, 311 mmol, 1.0 eq) and 4-toluolsulfonyl chloride (71.16 g, 373 mmol, 1.2 eq) in CHCl3 (1200 mL) was added a solution of potassium carbonate (146 g, 1056 mmol, 3.4 eq) in H2O (500 mL) at RT. The resulting mixture was stirred overnight and diluted with H2O (500 mL). The solid was collected by filtration, washed with water, dried in vacuo to afford the desired product 7-bromo-1,5-naphthyridin-2(1H)-one (C-4) (28.8 g, 41.2% yield). 1H NMR (300 MHz, DMSO-d6) δ: 11.90 (bs, 1H), 8.51 (s, 1H), 7.88 (d, J=9.6 Hz, 1H), 7.81 (s, 1H), 6.74 (d, J=9.6 Hz, 1H); ESI-MS m/z: 225.1 [M+H]+.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-183104cc9ae147708dd6cfe7d639ed5f
Source dataset
uspto-grants-2015_08
Patent number
US09096590B2

Reaction notes

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