Ammonia → 2-Carbethoxy-3-n-propyl-4,5-dimethylpyrrole

HRID 1834439Notes

Reaction equation

HRID 1834439 reaction equation
I.[PH2](O)=O.[C:5]([C:10]1[NH:11][C:12]([CH3:16])=[C:13]([CH3:15])[CH:14]=1)([O:7][CH2:8][CH3:9])=[O:6].[CH:17](=O)[CH2:18][CH3:19].N>O.C(O)(=O)C>[C:5]([C:10]1[NH:11][C:12]([CH3:16])=[C:13]([CH3:15])[C:14]=1[CH2:17][CH2:18][CH3:19])([O:7][CH2:8][CH3:9])=[O:6]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 527PropanalHCID 24841Hydrogen iodideHCID 137478Ethyl 4,5-dimethyl-1H-pyrrole-2-carboxylateHCID 4124402Phosphinic Acid

Product 1

HCID 135450592-Carbethoxy-3-n-propyl-4,5-dimethylpyrroleYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Hydriodic acid (d 1.95, 10 ml) was slowly added to 10 ml of stirred and cooled acetic acid; hypophosphorous acid (50%, 2 ml) was then added. 2-Carbethoxy-4,5-dimethylpyrrole (0.004 mol) was added to the mixture at room temperature followed by propionaldehyde (0.008 mol). The solution was stirred 21/2 h at ca. 25° C. then poured into 200 ml of water. This was made alkaline with ammonia, extracted with ether, and the ether was evaporated to leave the crude product. This was an oil which solidified after distillation (1 × 10-4 mm). It was recrystallized from aqueous ethanol, then from ethanol m.p. 101°-104° C. (lit. 102° C), yield 40%. ##STR68##

Workup

  1. stirringThe solution was stirred 21/2 h at ca. 25° C.
  2. extractionextracted with ether
  3. customthe ether was evaporated

Sources & evidence

ORD record
ord-ae507132a1404395a595714b4e951d65
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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