Ammonia → HCID 70357805, compound

HRID 1165832Notes

Reaction equation

HRID 1165832 reaction equation
Cl.N1C=CC=CC=1.[CH2:8]([C@:15]12[C@@H:28]3[N:29]([CH2:32][CH:33]4[CH2:35][CH2:34]4)[CH2:30][CH2:31][C@:20]41[C:21]1[C:22]([O:38][C@H:19]4[C:18](=[O:39])[CH2:17][CH2:16]2)=[C:23]([O:36]C)[CH:24]=[CH:25][C:26]=1[CH2:27]3)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N>>[CH2:8]([C@:15]12[C@@H:28]3[N:29]([CH2:32][CH:33]4[CH2:34][CH2:35]4)[CH2:30][CH2:31][C@:20]41[C:21]1[C:22]([O:38][C@H:19]4[C:18](=[O:39])[CH2:17][CH2:16]2)=[C:23]([OH:36])[CH:24]=[CH:25][C:26]=1[CH2:27]3)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10176127Pyridinium chloride2×HCID 70357583HCID 70357583, compound

Product 1

HCID 70357805HCID 70357805, compound

Conditions

Temperature
160 °C

Procedure

12.5 g of pyridine hydrochloride and 5.2 g (12 mMol) of the compound of example 3 are mixed at room temperature, and heated to 160° C. whilst stirring. After 1 hour, a further 12.5 g of pyridine hydrochloride are added, and heating continues for a further hour at 160° C. After cooling, the mixture is taken up in ice water, rendered basic with conc. ammonia and extracted three times with methylene chloride. The organic phases are dried over Na2SO4, concentrated by evaporation and flash-chromatographed over silica gel with ethyl acetate/hexane 1:3. The following are isolated: the title compound as a colorless oil and unreacted starting material. The title compound is converted into the hydrochloride with ether/ethanol/HCl: M.p.: 260° C.

Workup

  1. temperatureheating
  2. waitcontinues for a further hour at 160° C
  3. temperatureAfter cooling
  4. extractionextracted three times with methylene chloride
  5. dry with materialThe organic phases are dried over Na2SO4
  6. concentrationconcentrated by evaporation
  7. customflash-chromatographed over silica gel with ethyl acetate/hexane 1:3
  8. customThe following are isolated

Sources & evidence

ORD record
ord-db18e5775fd24acba06abebd543235ff
Source dataset
uspto-grants-1990_03
Patent number
US04912114

Reaction notes

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