Sodium Hydroxide → Ethyl 1-amino-1H-pyrrole-2-carboxylate

HRID 1261916Notes

Reaction equation

HRID 1261916 reaction equation
Cl[O-].[Na+].[CH2:4]([O:6][C:7]([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)=[O:8])[CH3:5].[OH-].[Na+].[Cl-].[NH4+:17]>O.[OH-].[NH4+].COC(C)(C)C>[CH2:4]([O:6][C:7]([C:9]1[N:10]([NH2:17])[CH:11]=[CH:12][CH:13]=1)=[O:8])[CH3:5]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 45082088Ethyl 1-amino-1H-pyrrole-2-carboxylateYield 95.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 14923Ammonium HydroxideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

2 M of Sodium hypochlorite in Water (750 mL) (10-14% solution) was added dropwise to a solution of 1H-Pyrrole-2-carboxylic acid ethyl ester (50.0 g, 359 mmol), 2-Methoxy-2-methylpropane (1000 mL), Aliquot 336 (12 g, 31 mmol), 7 M of Sodium hydroxide in Water (1030 mL), 8 M of Ammonium hydroxide in Water (330 mL) and Ammonium chloride (120 g, 2200 mmol). The reaction was immediately worked up upon complete addition of sodium hypochlorite. The organic layer was separated and was washed with saturated sodium thiosulfate (3×500 mL). Organic extracts (3×500 mL) were dried over magnesium sulfate, filtered and reduced to afford 53.0 grams 1-Amino-1H-pyrrole-2-carboxylic acid ethyl ester as a brown oil without further purification.

Workup

  1. customThe organic layer was separated
  2. washwas washed with saturated sodium thiosulfate (3×500 mL)
  3. dry with materialwere dried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-691fb23d675146688b3e4c5e981f9a2f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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