Hydrochloric Acid → HCID 67980981, compound

HRID 2406220Notes

Reaction equation

HRID 2406220 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:11]([CH:12]=[N:13][N:14]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Br:20]Br.Cl>O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:11]([C:12]([Br:20])=[N:13][N:14]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 24408BromineHCID 67054482HCID 67054482, compound

Product 1

HCID 67980981HCID 67980981, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4,5,7,8-tetrahydro-1,2,3a,6-tetraaza-azulene-6-carboxylic acid tert-butyl ester (200 mg, 0.839 mmol) in water was added 10N NaOH until a clear solution was formed. Br2 (0.432 mL, 8.39 mmol) was then added slowly while maintaining a pH of 12 by addition of conc. NaOH. The reaction was stirred at ambient temperature for 16 hours. The reaction mixture was then acidified to pH ˜4 with 6 M HCl. The organics were extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound as a white solid (185 mg, 70% yield).

Workup

  1. customwas formed
  2. temperaturewhile maintaining a pH of 12
  3. extractionThe organics were extracted three times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ae94b0dbed54b82bf36cd4f4406bebe
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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