Sodium Carbonate → HCID 14500635, compound

HRID 1761588Notes

Reaction equation

HRID 1761588 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[CH3:8].C(N1C=CC=C1C(O)C1C=CC=C(N)C=1)C.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO.C(O)(=O)C>[CH2:7]([N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[CH3:8]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 14500633HCID 14500633, compoundHCID 14500634HCID 14500634, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14500635HCID 14500635, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 1.5 g (39 mmol) of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature, a solution of 7.5 g (35 mmol) of 1-ethyl-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 carefuly 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 crude alcohol thus obtained, 1-ethyl-2-(3'-amino-α-hydroxybenzyl)pyrrole (7.5 g, 35 mmol) was dissolved in 100 ml of methanol, cooled to 0° C. and treated with 20 ml of glacial acetic acid and 4.7 g (78 mmol) of sodium cyanoborohydride. The reaction mixture was stirred at room temperature for 3 hours, poured into 600 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (3×250 ml), dried and evaporated in vacuo. The residue was purified by column chromatography on 500 g of silica gel, using hexane-ethyl acetate (80:20) as eluant, thus obtaining 5.9 g (84%) of 1-ethyl-2-(3'-aminobenzyl)pyrrole, the title compound, as an oil.

Workup

  1. additionwas added dropwise, at room temperature
  2. temperatureThe reaction mixture was refluxed for 15 minutes
  3. customthe excess reagent destroyed by carefuly 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
  6. customThe unstable crude alcohol thus obtained
  7. temperaturecooled to 0° C.
  8. extractionthe product extracted with ethyl acetate (3×500 ml)
  9. washThe combined extracts were washed with water (3×250 ml)
  10. customdried
  11. customevaporated in vacuo
  12. customThe residue was purified by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-1538d16058fe498f8c3cd408f7822cc8
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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