Sodium Carbonate → HCID 21873633, compound

HRID 639020Notes

Reaction equation

HRID 639020 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[N:11]=[CH:10][CH:9]=[C:8]3O.P(Br)(Br)[Br:17].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:17][C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]3[O:4][CH2:3][CH2:2][O:1][C:6]3=2)[N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 178516371HCID 178516371, compound

Product 1

HCID 21873633HCID 21873633, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-10-ol (2.8 g) in dry DMF (8 mL) was cooled in ice and phosphorus tribromide (0.7 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 (1.65 g, 90%). LC/MS (ES) m/z 267.

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-8faac6cb791a49719ae86a33bfedb806
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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