1H-Pyrrole-2-carboxylic acid, 3-amino-, ethyl ester Chemical Properties

Boiling point:

310.9±22.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

15.93±0.50(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C7H10N2O2/c1-2-11-7(10)6-5(8)3-4-9-6/h3-4,9H,2,8H2,1H3

InChIKey

SPNDLEQTZLQLTA-UHFFFAOYSA-N

SMILES

N1C=CC(N)=C1C(OCC)=O

Safety Information

HazardClass 

IRRITANT

1H-Pyrrole-2-carboxylic acid, 3-amino-, ethyl ester Usage And Synthesis

Uses

Ethyl 3-amino-1H-pyrrole-2-carboxylate

Synthesis

Step 2: Synthesis of ethyl 3-amino-1H-pyrrole-2-carboxylate A solution of diethyl 2-((2-cyanoethenyl)amino)malonate (30 g, 119.3 mmol, 1.00 equiv, 90% purity) in ethanol (420 mL) was added to a 1000 mL round bottom flask. Sodium ethoxide (80 mL, 21% w/w ethanol solution) was subsequently added. The reaction mixture was stirred at room temperature for 3 days. Upon completion of the reaction, the reaction was quenched by the addition of acetic acid (15 mL) and the mixture was subsequently concentrated under reduced pressure to remove the solvent. The concentrated residue was dissolved in dichloromethane (200 mL) and washed sequentially with saturated aqueous sodium bicarbonate (2 × 100 mL) and brine (1 × 100 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The residue was dried under high vacuum (HV) to give ethyl 3-amino-1H-pyrrole-2-carboxylate (10 g, 49% yield) as an orange slurry.

References

[1] Tetrahedron, 2014, vol. 70, # 31, p. 4631 - 4639
[2] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 128-129
[3] Journal of Organic Chemistry, 1999, vol. 64, # 22, p. 8411 - 8412
[4] Chemical Biology and Drug Design, 2011, vol. 78, # 6, p. 932 - 940

1H-Pyrrole-2-carboxylic acid, 3-amino-, ethyl ester(252932-48-2)Related Product Information

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• ETHYL 3-([3-(TRIFLUOROMETHYL)BENZOYL]AMINO)-1H-INDOLE-2-CARBOXYLATE
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• ETHYL 1-(4-CHLOROBENZYL)-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE
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• 3-AMINO-4-CYANO-1-PHENYL-1H-PYRROLE-2-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 3-[5-CYANO-2,4-DIOXO-3,4-DIHYDRO-1(2H)-PYRIMIDINYL]-1H-INDOLE-2-CARBOXYLATE
• ETHYL 1-BENZYL-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE
• ETHYL 1-(3-CHLOROBENZYL)-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE
• ethyl 3-amino-4-cyano-1-(propan-2-yl)-1H-pyrrole-2-carboxylate
• ETHYL 1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE
• ETHYL 1-(2,4-DICHLOROBENZYL)-3-((2,4-DICHLOROBENZYL)[3-(TRIFLUOROMETHYL)BENZOYL]AMINO)-1H-INDOLE-2-CARBOXYLATE
• ETHYL 1-(4-METHYLBENZYL)-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE
• ETHYL 3-((2-CYANO-3-[(ETHOXYCARBONYL)AMINO]-3-OXO-1-PROPENYL)AMINO)-1H-INDOLE-2-CARBOXYLATE
• ETHYL 1-(2-CHLOROBENZYL)-3-(1H-PYRROL-1-YL)-1H-INDOLE-2-CARBOXYLATE