Hydrogen Bromide → HCID 3078977, compound

HRID 727789Notes

Reaction equation

HRID 727789 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([N:24]([CH3:26])[CH3:25])[CH3:23])=[CH:16][CH:15]=1)[C:10](=[O:27])[CH2:9]3.Br>C(O)(=O)C>[F:1][C:2]1[CH:29]=[CH:28][C:5]2[CH2:6][CH2:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH:22]([N:24]([CH3:25])[CH3:26])[CH3:23])=[CH:18][CH:19]=1)[C:10](=[O:27])[CH:9]=3

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 3078979HCID 3078979, compound

Product 1

HCID 3078977HCID 3078977, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
50 °C

Procedure

To a mixture of 116 g of 9-fluoro-2-[4-(2-dimethylaminopropoxy)phenyl]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one and 1.2 l of acetic acid is added 116 ml of 30% hydrobromic acid--acetic acid. While the solution is heated to 50° C., a solution of 48 g of hydrobromic acid and 200 ml of acetic acid is added dropwise over the period of 30 minutes. After the completion of the dropwise addition, the mixture is stirred for further 30 minutes. The solvent is distilled off under reduced pressure. Water and ethyl acetate are added to the residue, and the mixture is rendered alkaline with potassium carbonate. The ethyl acetate layer is separated, washed with water and extracted with an aqueous solution of hydrochloric acid. The hydrochloric acid layer is rendered alkaline with potassium carbonate, and the resultant oily substance is dissolved in ethyl acetate, which is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure. Ethanol and fumaric acid are added to the residue to convert it into its salt. The resultant crystals are collected by filtration and recrystallized from water--ethanol to give 9-fluoro-2-[4-(2-dimethylaminopropoxy)phenyl]-5,6-dihydrobenzo[h]cinnolin-3(2H)-one.fumarate, m.p. 178°-180° C.

Workup

  1. additionAfter the completion of the dropwise addition
  2. distillationThe solvent is distilled off under reduced pressure
  3. additionWater and ethyl acetate are added to the residue
  4. customThe ethyl acetate layer is separated
  5. washwashed with water
  6. extractionextracted with an aqueous solution of hydrochloric acid
  7. dissolutionthe resultant oily substance is dissolved in ethyl acetate
  8. washwhich is washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThe solvent is distilled off under reduced pressure
  11. additionEthanol and fumaric acid are added to the residue
  12. filtrationThe resultant crystals are collected by filtration
  13. customrecrystallized from water

Sources & evidence

ORD record
ord-257675a9feaf4faca9b84b720cc0e84b
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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