Hydrogen Bromide → HCID 69830648, compound

HRID 1275672Notes

Reaction equation

HRID 1275672 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([NH:18][N:19]3[CH2:23][CH2:22][N:21]=[CH:20]3)[CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][CH2:9]1)=O)(C)(C)C.Br>CO.C(O)(=O)C>[N:19]1([NH:18][C:12]2[CH:13]=[CH:14][C:15]([CH3:17])=[C:16]3[C:11]=2[CH2:10][CH2:9][NH:8]3)[CH2:23][CH2:22][N:21]=[CH:20]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 69830908HCID 69830908, compound

Product 1

HCID 69830648HCID 69830648, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

1-t-Butoxycarbonyl-2,3-dihydro-4-(2-imidazolinylamino)-7-methylindole (0.384 g, 1.22 mmol) is dissolved in methanol (10 mL). To this solution is added 30% hydrogen bromide in acetic acid (2.5 mL). The solution is heated to reflux for 2.5 hours. The reaction mixture is concentrated by rotary evaporation and the resulting orange liquid taken up in chloroform. The chloroform solution is treated with 50% NaOH solution and extracted with three 25 mL portions of chloroform. The organic layers are collected and dried over anhydrous potassium carbonate. Filtration and removal of the solvent produces a brownish-orange solid which is purified via silica gel column chromatography using 10% methanol (ammonium hydroxide treated)/methylene chloride as the eluent to afford 0.257 g of 2,3-dihydro-4-(2-imidazolinylamino)-7-methylindole as a light-orange solid.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 2.5 hours
  3. concentrationThe reaction mixture is concentrated by rotary evaporation
  4. additionThe chloroform solution is treated with 50% NaOH solution
  5. extractionextracted with three 25 mL portions of chloroform
  6. customThe organic layers are collected
  7. dry with materialdried over anhydrous potassium carbonate
  8. filtrationFiltration and removal of the solvent
  9. customproduces a brownish-orange solid which
  10. customis purified via silica gel column chromatography

Sources & evidence

ORD record
ord-d0e94f34029140e78a756aa43e72dbe6
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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