Sodium Carbonate → HCID 59026172, compound

HRID 639018Notes

Reaction equation

HRID 639018 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1O)=[C:9]1[O:13][CH2:14][CH2:15][O:16][C:8]1=[CH:7][CH:6]=2.P(Br)(Br)[Br:18].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:18][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:16][CH2:15][CH2:14][O:13][C:9]3=2)[N:4]=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 178516336HCID 178516336, compound

Product 1

HCID 59026172HCID 59026172, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Chloro-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-10-ol (3.12 g, 13.1 mmol) in dry DMF (16.7 mL) was cooled in ice and phosphorus tribromide (4.78 mL) added drop-wise, and the mixture was stirred, with ice-cooling for 30 minutes then allowed to warm to room temperature and stirred for a further 2 hours. It was cooled in ice and sodium carbonate solution was added and the solid was collected, washed well with water, and dried in vacuo, to afford a pale yellow solid (3.55 g, 90%). LC/MS (ES) m/z 300 (MH+ 100%); 1H-NMR (400 MHz, DMSO), 8.73 (1H, s, CHNHC), 7.62 (1H, d, J=9.12, CHCOCH2), 7.47 (1H, d, J=9.08, CHCN), 4.43 (4H, m, 2×(CH2O)).

Workup

  1. temperaturecooling for 30 minutes
  2. stirringstirred for a further 2 hours
  3. temperatureIt was cooled in ice
  4. customthe solid was collected
  5. washwashed well with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c914e6bf972e48778d6f018ecfec0949
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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