HCID 14500628, compound → HCID 14500629, compound

HRID 1761585Notes

Reaction equation

HRID 1761585 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1>O1CCCC1>[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]([OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1

Participants

4

Reactant 2

HCID 14500628HCID 14500628, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14500629HCID 14500629, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2 g (50 mmol) of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature and under nitrogen atmosphere, a solution of 9 g (45 mmol) of 1-methyl-2-(3'-aminobenzoyl)pyrrole in 100 ml of anhydrous tetrahydrofuran. The reaction mixture was refluxed for 15 minutes, cooled to 0° C. and the excess reagent destroyed by carefully adding ethyl acetate, saturated sodium sulfate solution and solid anhydrous sodium sulfate. The insoluble material was separated by filtration and the filtrate evaporated in vacuo. The unstable 1-methyl-2-(3'-amino-α-hydroxybenzyl)pyrrole thus obtained (9 g, 45 mmol) was dissolved in 150 ml of methanol, cooled to 0° C. and treated with 24 ml (419 mmol) of glacial acetic acid and 5.67 g (90 mmol) of sodium cyanoborohydride. The reaction mixture was stirred at room temperature for 18 hours, poured into 500 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (3×300 ml), dried and evaporated in vacuo. The residue was purified by column chromatography on 600 g of silica gel, using hexane-ethyl acetate (80:20) as eluant, obtaining 4.89 g (67%) of the title compound, 1-methyl-2-(3'-aminobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Workup

  1. additionwas added dropwise, at room temperature and under nitrogen atmosphere
  2. temperatureThe reaction mixture was refluxed for 15 minutes
  3. customthe excess reagent destroyed by carefully adding ethyl acetate, saturated sodium sulfate solution and solid anhydrous sodium sulfate
  4. customThe insoluble material was separated by filtration
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-eda7fc5eb8f442dc9c23c6cb89106668
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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