Ammonium Hydroxide → HCID 5055125, compound

HRID 1834429Notes

Reaction equation

HRID 1834429 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:13][CH:14]1OC(C)OC(C)O1.[I-].[PH4+].[OH-].[NH4+]>I.C(OC(=O)C)(=O)C.[PH2](O)=O>[CH3:1][C:2]1[NH:3][C:4]([CH2:13][CH3:14])=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 31264ParaldehydeHCID 137481Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylateHCID 166618Phosphonium iodide ((PH4)I)

Product 1

HCID 5055125HCID 5055125, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 7918Acetic AnhydrideSolventHCID 24841Hydrogen iodideSolventHCID 4124402Phosphinic AcidSolvent

Procedure

2,4-Dimethyl-3-carbethoxy-pyrrole (0.668 g) was dissolved in a mixture of hydriodic acid (10 ml), acetic anhydride (10 ml) and hypophosphorous acid (2 ml). Paraldehyde (0.75 ml) was added. The solution was stirred 5 min., decolorized with phosphonium iodide, and poured into ice water. The cooled mixture was brought to pH 8 with ammonium hydroxide. The product was filtered off and distilled (90°-100°, 5 × 10-4 mm), giving colourless crystals (53%), m.p. 108°-109° after changing to prisms at 105°. For analysis, it was recrystallized from hexane as prismatic rods, m.p. 107°-109° (lit17) 106°-107°).

Workup

  1. filtrationThe product was filtered off
  2. distillationdistilled (90°-100°, 5 × 10-4 mm)

Sources & evidence

ORD record
ord-a988550e61104924bc29383beb0b54e5
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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