Ammonia → HCID 14582066, compound

HRID 1165831Notes

Reaction equation

HRID 1165831 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:24][CH2:23][C@:12]34[C:13]5[C:14]6[O:22][C@H:11]3[C:10](=[O:25])[CH2:9][CH2:8][C@@:7]4([CH2:26][CH3:27])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20]C)[CH2:3][CH2:2]1.Cl.N1C=CC=CC=1.N>O>[CH:1]1([CH2:4][N:5]2[CH2:24][CH2:23][C@:12]34[C:13]5[C:14]6[O:22][C@H:11]3[C:10](=[O:25])[CH2:9][CH2:8][C@@:7]4([CH2:26][CH3:27])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10176127Pyridinium chlorideHCID 70357827HCID 70357827, compound

Product 1

HCID 14582066HCID 14582066, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.25 g (8.9 mMol) of the compound of example 1 and 10 g of pyridine hydrochloride are heated for 3 hours to 190° C., then taken up in water after cooling, rendered basic with conc. ammonia, and extracted three times with methylene chloride. Flash-chromatography with ethyl acetate/hexane 1:5 yields the title compound as colorless crystals. Recrystallization from ether/pentane yields an analysis-pure product: M.p.: 157°-158° C.

Workup

  1. temperatureafter cooling
  2. extractionextracted three times with methylene chloride

Sources & evidence

ORD record
ord-b327aefc22db405da7f2bbc071db77bb
Source dataset
uspto-grants-1990_03
Patent number
US04912114

Reaction notes

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