Ammonia → 3-Hydroxy-2-oxo-4-propionyl-2,5-dihydropyrrole

HRID 1720951Notes

Reaction equation

HRID 1720951 reaction equation
[O:1]=[C:2]([CH2:8][C:9](=[O:12])[CH2:10][CH3:11])[C:3]([O:5]CC)=O.[Cl-].C[C:15](=[NH2+:17])C.N>>[OH:1][C:2]1[C:3](=[O:5])[NH:17][CH2:15][C:8]=1[C:9](=[O:12])[CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 61590Ethyl-2,4-dioxohexanoateHCID 21939857Dimethylmethyleneammonium chloride

Product 1

HCID 233554373-Hydroxy-2-oxo-4-propionyl-2,5-dihydropyrrole

Procedure

Reaction of ethyl 2,4-dioxohexanoate with dimethylmethylene ammonium chloride and ammonia, analogous to the procedure in Preparation 8, gave the title compound as an amorphous solid. 1H nmr (250 MHz, DMSO-d6) δ 0.99 (t, J=7.3 Hz, 3H), 2.75 (q, J=7.3 Hz, 2H), 3.81 (s, 2H), 8.84 (s, 1H).

Workup

  1. customanalogous to the procedure in Preparation 8

Sources & evidence

ORD record
ord-27439ca9faa140dd8d4a05a28dc3d3db
Source dataset
uspto-grants-1996_04
Patent number
US05508300

Reaction notes

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