Hydrogen Bromide → HCID 13050889, compound

HRID 1702595Notes

Reaction equation

HRID 1702595 reaction equation
Br.BrBr.Br[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([O:15][CH2:16][CH3:17])[C:9](C(=O)C)=[C:8]2[O:21][CH3:22].[N-:23]=[N+:24]=[N-:25].[Na+].[C:27](OCC)(=[O:29])[CH3:28]>CCCCCC.O.CN(C)C=O.C(O)(=O)C.CCOCC>[N:23]([CH2:28][C:27]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([O:15][CH2:16][CH3:17])[CH:9]=[C:8]2[O:21][CH3:22])=[O:29])=[N+:24]=[N-:25]

Participants

11

Reactant 5

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 24408BromineHCID 33557Sodium AzideHCID 20525717HCID 20525717, compound

Product 1

HCID 13050889HCID 13050889, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4.91 gm. (20 mmoles) of B in 270 ml. of acetic acid and 75 ml. of ether, cooled to 10° C., was added gaseous HBr in excess. A solution of 3.4 gm. (21 mmoles) of bromine in 75 ml. acetic acid was added over 75 min. The resulting mixture was stirred for 1 hour at 22° C., evaporated and the residue stirred with 150 ml. of 10% NaHCO3. The aqueous suspension was extracted with 3×200 mls. of CHCl3 and after drying and evaporation of the organic extracts there was obtained 6.57 gm. of crude 6-bromo-acetyl-2-ethoxy-4-methoxy quinoline. This material was dissolved in 150 ml. of dimethylformamide and to the solution was added a solution of 1.95 gm. (30 mmoles) of sodium azide in 35 ml. of H2O. The solution temperature rose from 22° C. to 35° C. and after 105 minutes had fallen back to 25° C. The mixture was diluted with 1500 ml. of water and extracted with 3×300 ml. of CHCl3. After washing the organic extracts with water (3×200 ml.), drying and evaporation, there was obtained 5.95 gm. of crude solid. This was dissolved in 75 ml. of ethyl acetate, 50 ml. of hexane was added, and after refrigeration and filtration, there was obtained 4.88 gm. (85%) of c, m.p. 129°-132° C.

Workup

  1. customevaporated
  2. stirringthe residue stirred with 150 ml
  3. extractionThe aqueous suspension was extracted with 3×200 mls
  4. dry with materialof CHCl3 and after drying
  5. customevaporation of the organic extracts
  6. customthere was obtained 6.57 gm
  7. dissolutionThis material was dissolved in 150 ml
  8. waitThe solution temperature rose from 22° C. to 35° C. and after 105 minutes
  9. customhad fallen back to 25° C
  10. additionThe mixture was diluted with 1500 ml
  11. extractionof water and extracted with 3×300 ml
  12. washAfter washing the organic extracts with water (3×200 ml.)
  13. customdrying
  14. customevaporation
  15. customthere was obtained 5.95 gm
  16. dissolutionThis was dissolved in 75 ml
  17. filtrationafter refrigeration and filtration
  18. customthere was obtained 4.88 gm

Sources & evidence

ORD record
ord-fbfb1d66b0204e399715a66fc929bd45
Source dataset
uspto-grants-1982_09
Patent number
US04348398

Reaction notes

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