Acetic Acid → HCID 70021476, compound

HRID 1275653Notes

Reaction equation

HRID 1275653 reaction equation
C(O)(=O)C.C(OC([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH:22][N:23]3[CH2:27][CH2:26][N:25]=[CH:24]3)[C:19]=2[CH3:21])[CH2:14][CH2:13]1)=O)(C)(C)C.Br.C(O)(=O)C.CO>C(Cl)Cl>[N:23]1([NH:22][C:18]2[C:19]([CH3:21])=[C:20]3[C:15]([CH2:14][CH2:13][NH:12]3)=[CH:16][CH:17]=2)[CH2:27][CH2:26][N:25]=[CH:24]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 887MethanolHCID 70158620HCID 70158620, compound

Product 1

HCID 70021476HCID 70021476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-t-butoxycarbonyl-2,3-dihydro-6-(2-imidazolinylamino)-7-methylindole acetic acid salt (0.69 g, 1.85 mmol) in methylene chloride (7 mL) is treated dropwise with a 30% solution of hydrogen bromide in acetic acid (1.0 g, 3.7 mmol). A precipitate forms which dissolves upon addition of 2 mL of methanol. The reaction is stirred for 2.5 hours then concentrated under a stream of nitrogen. The material is diluted with water, and chloroform and brought to pH=14 with 1 M aqueous sodium hydroxide solution. The chloroform layer is collected and the aqueous solution extracted two additional times with chloroform. The combined organic extracts are dried over potassium carbonate, filtered and the filtrate evaporated on a rotary evaporator to afford 2,3-dihydro-6-(2-imidazolinylamino)-7-methylindole.

Workup

  1. concentrationthen concentrated under a stream of nitrogen
  2. additionThe material is diluted with water, and chloroform
  3. customThe chloroform layer is collected
  4. extractionthe aqueous solution extracted two additional times with chloroform
  5. dry with materialThe combined organic extracts are dried over potassium carbonate
  6. filtrationfiltered
  7. customthe filtrate evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-9f5d02954f8d4ecebbbcdc2ef47f47bd
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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