HCID 86654673, compound → HCID 66914943, compound

HRID 880461Notes

Reaction equation

HRID 880461 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]1[CH3:17])=[N+]=[N-]>CO.[C].[Pd]>[CH3:17][C:7]1[N:6]([CH2:5][CH2:4][NH2:1])[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 86654673HCID 86654673, compound

Product 1

HCID 66914943HCID 66914943, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (100 mg) was added to a solution of 1-(2-azidoethyl)-2-methyl-4-phenyl-pyrrole (640 mg, 2.96 mmol) in methanol (20 mL) at room temperature and hydrogenated at atmospheric pressure for 27 h. The catalyst was filtered and washed with methanol (20 mL). The combined filtrate and washings were concentrated in vacuo to afford 2-(2-methyl-4-phenyl-pyrrol-1-yl)ethanamine (490 mg, 83%) as a brown syrup.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol (20 mL)
  3. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-e189c794785c4e55a2cf0eadd138a912
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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